Benzene → N-(2-[4-Carbomethoxyphenyl]ethyl)-2-hydroxy-2-phenylethanamine

HRID 1633091Notes

Reaction equation

HRID 1633091 reaction equation
[C:1]1([C:7]([CH:9]=O)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12].C1C=CC=CC=1>O>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH:23][CH2:9][CH:7]([OH:8])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:17][CH:16]=1)([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 241BenzeneHCID 14090PhenylglyoxalHCID 11183521Methyl 4-(2-aminoethyl)benzoate

Product 1

HCID 20134176N-(2-[4-Carbomethoxyphenyl]ethyl)-2-hydroxy-2-phenylethanamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Phenyl glyoxal (0.8 g) and 2-(4-carbomethoxyphenyl) ethanamine (1.1 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 and sodium borohydride (2.0 g) was added portionwise with ice cooling. The mixture was stirred for 2 hours, the solvent was evaporated and the residue was partitioned between water and ethyl acetate. The dried organic extract was evaporated and crystallised from benzene/hexane, mp 105°-106°. (CDCl3) 6.80-7.60 (8H, m), 6.18 (3H, s), 5.34 (1H, m), 2.94 (2H, d, J=8 Hz), 2.77 (5H, m), 2.09 (2H, d, J=8 Hz).

Workup

  1. customhad been collected
  2. additionwas added portionwise with ice cooling
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. extractionThe dried organic extract
  6. customwas evaporated
  7. customcrystallised from benzene/hexane, mp 105°-106°

Sources & evidence

ORD record
ord-9551cf2a13234a80ac91cecef77204c5
Source dataset
uspto-grants-1984_10
Patent number
US04478849

Reaction notes

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