Triethylamine → 3-[(S)-1-(4-Chloro-phenyl)-ethylamino]-1-phenyl-propan-1-one

HRID 473928Notes

Reaction equation

HRID 473928 reaction equation
CCN(CC)CC.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH2:17])[CH3:16])=[CH:11][CH:10]=1.Cl[CH2:19][CH2:20][C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:22]>O1CCCC1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][CH2:19][CH2:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])[CH3:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702953-ChloropropiophenoneHCID 1550852(S)-(-)-1-(4-chlorophenyl)ethylamine

Product 1

HCID 581093723-[(S)-1-(4-Chloro-phenyl)-ethylamino]-1-phenyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NEt3 (60 mL) followed by (S)-1-(4-chloro-phenyl)-ethylamine (20.5 g) was added to a solution of 3-chloro-1-phenyl-propan-1-one (23.2 g) in tetrahydrofuran (200 mL). The resulting mixture was stirred at room temperature overnight. Then, the solution was concentrated, water (100 mL) was added to the residue, and the resulting mixture was extracted with tert-butyl methyl ether. The combined organic extracts were washed with water and brine and dried (MgSO4). The title compound was obtained after removal of the solvent.

Workup

  1. concentrationThen, the solution was concentrated
  2. additionwater (100 mL) was added to the residue
  3. extractionthe resulting mixture was extracted with tert-butyl methyl ether
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-58c106b7eeb24413a024fa981fbea97e
Source dataset
uspto-grants-2014_01
Patent number
US08637505B2

Reaction notes

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