Ammonia → HCID 19775335, compound

HRID 1613182Notes

Reaction equation

HRID 1613182 reaction equation
[ClH:1].Br[CH2:3][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][N:9]([C:11]([CH3:28])([CH3:27])[CH2:12][O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:10])=[CH:6][CH:5]=1.[NH3:31]>>[ClH:1].[ClH:1].[NH2:31][CH2:3][C:4]1[CH:30]=[CH:29][C:7]([CH2:8][N:9]([C:11]([CH3:28])([CH3:27])[CH2:12][O:13][CH:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:10])=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 19775305HCID 19775305, compound

Product 1

HCID 19775335HCID 19775335, compoundYield 45%

Procedure

A solution of 2-[N-(4-bromomethylbenzyl)-N-methylamino]-1-diphenylmethoxy-2-methylpropane hydrochloride (800 mg -- see Example 23) in saturated methanolic ammonia (40 ml) was stirred at room temperature for 18 hours and evaporated. The residue was purified by chromatography on silica (5 g) using methylene chloride plus 0-2% methanol as the eluant. Appropriate fractions were combined and evaporated to give the free base of the title compound (310 mg, 45%) as a colourless oil which was used directly in Example 47. A small portion of the residue was dissolved in ether and the solution was treated with excess saturated ethereal hydrogen chloride. The resulting precipitated oil was collected and triturated with acetone to give the title compound as a colourless foam.

Workup

  1. customevaporated
  2. customThe residue was purified by chromatography on silica (5 g)
  3. customevaporated

Sources & evidence

ORD record
ord-1dd842fde08b4d0d986c27296632632f
Source dataset
uspto-grants-1993_03
Patent number
US05192765

Reaction notes

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