Processes for the preparation of aminoethoxybenzyl alcohols

A process for preparing a compound of Formula I:

• wherein:
• R1 and R2 are each, independently, selected from the group consisting of C1-C12 alkyl, heteroaryl and aryl;
• or
• R1 and R2 together form a group of formula —(CH2)n— that is optionally substituted with from 1-3 substituents selected from the group consisting of CN, NO2, C1-6 alkyl, C3-7 cycloalkyl, aryl, heteroaryl, halogen, OH, NR5R5′, CHO, COOR5, CONR5R5′, SR5, —O-aryl and —O-heteroaryl;
• R3 is selected from the group consisting of H, C1 alkyl, C3-7 cycloalkyl, aryl, heteroaryl, CN, NO2 and halogen;
• R5 and R5 are each, independently, H or C1 alkyl;
• and
• n is 2, 3, 4, 5, 6 or 7;
• comprising reacting a phenoxyacetamide of Formula VI:
• wherein R4 is H or C1-6 alkoxy;
• with a reducing agent for a time and under conditions effective to form said compound of Formula I;
• wherein optionally the phenoxyacetamide of Formula VI is formed by a process comprising:
• a) reacting an α-haloacetamide of Formula IV:
• wherein X1 is Cl or Br;
• and
• wherein optionally the α-haloacetamide of Formula IV is formed by a process comprising:
• i) reacting an acid halide of Formula II:
• wherein X1 and X2 are each, independently, Cl or Br;
• with an amine of Formula III:
• for a time and under conditions effective to form an α-haloacetamide of Formula IV:
• b) with a compound of Formula V:
• wherein R4 is H or C1-6 alkoxy;
• in the presence of base and optionally in the presence of a phase transfer catalyst for a time and under conditions effective to form the phenoxyacetamide of Formula VI.