Hydroxylamine → HCID 19865869, compound

HRID 1199825Notes

Reaction equation

HRID 1199825 reaction equation
Br[CH:2]([CH3:17])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=2)[CH:6]=1)=[O:4].[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+].NO>>[CH2:18]([N:25]1[CH2:30][CH2:29][N:28]([CH:2]([CH3:17])[C:3]([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:15][CH3:16])[CH:11]=3)[CH:6]=2)=[O:4])[CH2:27][CH2:26]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 4

HCID 787HydroxylamineHCID 759941-BenzylpiperazineHCID 4311764Sodium borohydrideHCID 127563272-Bromo-1-(6-methoxynaphthalen-2-yl)propan-1-one

Product 1

HCID 19865869HCID 19865869, compoundYield 54%

Procedure

From 2-bromo-1-(6-methoxy-2-naphtyl)-1-propanone and 1-benzylpiperazine, the compound 2-(4-benzyl-1-piperazinyl)-1-(6-methoxy-2-naphtyl)-1-propanone is prepared (MG 14256; m.p. 89°-91° C., which is reduced with NaBH4 to the corresponding amino alcohol as a mixture of the two stereoisomeric forms which are separated by flash chromatography.

Workup

  1. customare separated by flash chromatography

Sources & evidence

ORD record
ord-552b72f8e98e48bbb943a352d6dc8adc
Source dataset
uspto-grants-1990_02
Patent number
US04902799

Reaction notes

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