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

HRID 1906944Notes

Reaction equation

HRID 1906944 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). EXAMPLE 26

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-5105358bfa1d4d5da53279fdbb99dfa9
Source dataset
uspto-grants-1987_03
Patent number
US04654371

Reaction notes

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