Ammonia → (S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

HRID 2388362

Reaction equation

HRID 2388362 reaction equation
C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC(OC)=CC=1)(O)C(O)=O)(=O)C1C=CC(OC)=CC=1.[CH3:31][N:32]([CH3:52])[CH2:33][CH2:34][C@H:35]([O:41][C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1)[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1.O.N>ClCCl>[CH3:52][N:32]([CH3:31])[CH2:33][CH2:34][C@H:35]([O:41][C:42]1[C:51]2[C:46](=[CH:47][CH:48]=[CH:49][CH:50]=2)[CH:45]=[CH:44][CH:43]=1)[C:36]1[S:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 131729950(s)-n,n-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-anisoyl-l-tartarate salt

Product 1

HCID 9818212(S)-(+)-N,N-Dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The (S)—N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine di-p-anisoyl-L-tartarate salt (9a) (100 gm) was added to biphasic solvent mixture of water (500 ml) and dichloromethane (250 ml). To the slurry aqueous ammonia was added to adjust the pH to 10.8 and stirred further for 15-30 minutes. Organic layer was separated, washed with water, brine and concentrated to get thick oily mass of (S)-(+)-N,N-dimethyl-3-(1-naphthalenyloxy)-3-(2-thienyl)propanamine (6a). Yield: 44 gm.

Workup

  1. customOrganic layer was separated
  2. washwashed with water, brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-be9844340aca479bb9f7311c5480e66c
Source dataset
uspto-grants-2012_09
Patent number
US08269023B2

Linked notes

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