# US 4,396,765 A · Amino-1-[(halophenyl)-lower-alkyl]piperidines

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- Number: US 4,396,765 A
- Document ID: US4396765A
- Status: Granted
- Kind: A
- Application number: 06/363,268
- Filed: 1982-03-29
- Granted: 1983-08-02
- Earliest claimed: 1980-11-19
- Assignees: Sterling Drug Inc.
- Inventors: Bernard L. Zenitz
- Web page: https://patentgrep.com/patent/US4396765A

## CPC

- C07D 309/04: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07C 29/14: of a —CHO group
- C07C 45/00: Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07D 211/26: with hydrocarbon radicals, substituted by nitrogen atoms
- C07D 211/58: attached in position 4
- C07D 213/38: having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH.sub.2).sub.n -N.dbd.B]-substituted-piperidines useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate substituted piperidine with a (3- or 4-benzoylphenyl)-lower-alkyl halide or tosylate; by reaction of a 1-[2-(3- or 4-lithiophenyl)-lower-alkyl]-[(CH.sub.2).sub.n -N.dbd.B]-substituted-piperidine with benzonitrile and hydrolysis of the resulting benzimidoyl compound; or by reduction of a 1-[.alpha.-(3- or 4-benzoylphenyl)-lower-alkanoyl]-[(CH.sub.2).sub.n -N.dbd.B]-substituted-piperidine. The analogous carbinols are prepared by reduction, with an alkali metal borohydride, of the ketone.

## Claims

### Claim 1

A member of the group consisting of a compound having the formula ##STR7## where R is hydrogen or lower-alkyl; n is the integer 1; N.dbd.B is 1-piperidinyl or 4-morpholinyl; and Hal is halogen attached to the 3- or 4-position of the phenyl ring; and (B) acid-addition salts thereof.

### Claim 2 (depends on 1)

A compound according to claim 1 where the group Hal is attached to the 3-position of the phenyl ring.

### Claim 3 (depends on 2)

A compound according to claim 2 where N.dbd.B is 1-piperidinyl.

### Claim 4 (depends on 2)

A compound according to claim 2 where N.dbd.B is 4-morpholinyl.

### Claim 5 (depends on 3)

1-[2-(3-Bromophenyl)propyl]-4-(1-piperidinylmethyl)piperidine dihydrochloride according to claim 3.

### Claim 6 (depends on 3)

1-[2-(3-Bromophenyl)propyl]-3-(1-piperidinylmethyl)piperidine dihydrochloride according to claim 3.

### Claim 7 (depends on 3)

1-[2-(3-Bromophenyl)propyl]-2-(1-piperidinylmethyl)piperidine according to claim 3.

### Claim 8 (depends on 4)

1-[2-(3-Bromophenyl)propyl]-4-(4-morpholinylmethyl)piperidine dihydrochloride according to claim 4.

### Claim 9 (depends on 4)

1-[2-(3-Bromophenyl)propyl]-2-(4-morpholinylmethyl)piperidine dihydrochloride according to claim 4.