Dimethylamine → 1-Butanamine, 4-(2-(2-(2-chlorophenyl)ethyl)phenoxy)-N,N-dimethyl-, hydrochloride

HRID 2285537Notes

Reaction equation

HRID 2285537 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21].[CH3:22][NH:23][CH3:24]>O1CCCC1>[ClH:21].[CH3:22][N:23]([CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 205450052-(4-Bromobutoxy)-2'-chlorobibenzyl

Product 1

HCID 30553461-Butanamine, 4-(2-(2-(2-chlorophenyl)ethyl)phenoxy)-N,N-dimethyl-, hydrochlorideYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3.0 g of 2-(4-bromobutoxy)-2'-chlorobibenzyl in 15 ml of 50% aqueous dimethylamine solution and 15 ml of tetrahydrofuran was stirred at room temperature for 5 hours. The reaction mixture was concentrated and to the concentrate was added 2 N-NaOH solution. The product was extracted with ether, washed well with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. To the ether solution was added 20% ethanolic hydrogen chloride to yield white crystals. Recrystallization from ethanol-ether gave 2.8 g (93% yield) of 2-(4-dimethylaminobutoxy)-2'-chlorobibenzyl hydrochloride, m.p. 122°-123° C.

Workup

  1. concentrationThe reaction mixture was concentrated and to the concentrate
  2. additionwas added 2 N-NaOH solution
  3. extractionThe product was extracted with ether
  4. washwashed well with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. additionTo the ether solution was added 20% ethanolic hydrogen chloride
  7. customto yield white crystals
  8. customRecrystallization from ethanol-ether

Sources & evidence

ORD record
ord-aff028e2565840c482cd64f53b57f984
Source dataset
uspto-grants-1982_04
Patent number
US04323568

Reaction notes

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