Benzene → N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(3-chlorophenyl)-2-hydroxyethanamine

HRID 1065250Notes

Reaction equation

HRID 1065250 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([CH:10]=O)=[O:9])[CH:5]=[CH:6][CH:7]=1.[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][NH2:24])=[CH:18][CH:17]=1)([O:14][CH3:15])=[O:13].[CH:25]1C=CC=CC=1>O>[C:12]([C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH:23]([NH:24][CH2:10][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[OH:9])[CH3:25])=[CH:18][CH:17]=1)([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 11183521Methyl 4-(2-aminoethyl)benzoateHCID 124638932-(3-Chlorophenyl)-2-oxoacetaldehyde

Product 1

HCID 14279407N-(2-[4-Carbomethoxyphenyl]-1-methylethyl)-2-(3-chlorophenyl)-2-hydroxyethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Chlorophenylglyoxal (1.6 g) and 2-(4-carbomethoxyphenyl)ethanamine (1.8 g) were heated in refluxing benzene (100 ml) under a Dean and Stark head until the theoretical amount of water had been collected. The solvent was replaced with methanol (100 ml) and sodium borohydride (2.5 g) was added portionwise with ice cooling. The mixture was stirred for 2 h, the solvent was evaporated and the residue was paritioned between water (100 ml) and chloroform (100 ml). The dried organic extract was evaporated and crystallised from methanol to give a single diastereoisomer m.p. 94°-96° (0.19 g) (less active diasteroisomer).

Workup

  1. customhad been collected
  2. additionwas added portionwise with ice cooling
  3. customthe solvent was evaporated
  4. extractionThe dried organic extract
  5. customwas evaporated
  6. customcrystallised from methanol
  7. customto give a single diastereoisomer m.p. 94°-96° (0.19 g) (less active diasteroisomer)

Sources & evidence

ORD record
ord-3b89bfc3422d40f4bb35a1e866f1b693
Source dataset
uspto-grants-1982_05
Patent number
US04329358

Reaction notes

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