Sodium borohydride → 1-[2-Thienyl]-3-[1-(2-[1,4-benzodioxan-2-yl]-2-hydroxyethyl)piperid-4-yl]urea

HRID 225149Notes

Reaction equation

HRID 225149 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[NH:6][C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]([CH:19]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[O:21][CH2:20]2)=[O:18])[CH2:12][CH2:11]1)=[O:8].N1CCC(NC(NC2SC=CC=2)=O)CC1.BrCC(C1OC2C=CC=CC=2OC1)=O.[BH4-].[Na+]>CN(C=O)C.CCN(CC)CC.[OH-].[Na+]>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[NH:6][C:7]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH:17]([CH:19]2[O:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[O:21][CH2:20]2)[OH:18])[CH2:12][CH2:11]1)=[O:8]

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-oneHCID 233290711-(Piperid-4-yl)-3-(2-thienyl)ureaHCID 233290751-[2-Thienyl]-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]urea

Product 1

HCID 233290771-[2-Thienyl]-3-[1-(2-[1,4-benzodioxan-2-yl]-2-hydroxyethyl)piperid-4-yl]urea

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 22056947triethylamine N,N-dimethylformamideSolvent

Procedure

1-[2-Thienyl]-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]urea, prepared by reacting 1-(piperid-4-yl)-3-(2-thienyl)urea with 2-bromoacetyl-1,4-benzodioxan in DMF/Et3N, may be reduced using sodium borohydride in 2 N sodium hydroxide to give the title compound.

Sources & evidence

ORD record
ord-80ec1243b557497fb4553e67a7aaaf5a
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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