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

HRID 80947

Reaction equation

HRID 80947 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-b09480803c8b4742aeba444bd87fdb27
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Linked notes

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