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

HRID 225148Notes

Reaction equation

HRID 225148 reaction equation
[CH:1]1([C:7]([NH:9][C:10]([NH:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][C:20]([CH:22]3[O:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[O:24][CH2:23]3)=[O:21])[CH2:15][CH2:14]2)=[O:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C(NC(NC2CCNCC2)=O)=O)CCCCC1.BrCC(C1OC2C=CC=CC=2OC1)=O.[BH4-].[Na+]>CN(C=O)C.CCN(CC)CC.[OH-].[Na+]>[CH:1]1([C:7]([NH:9][C:10]([NH:12][CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH:20]([CH:22]3[O:27][C:26]4[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=4[O:24][CH2:23]3)[OH:21])[CH2:17][CH2:18]2)=[O:11])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 126085852-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-oneHCID 233290701-Cyclohexylcarbonyl-3-(piperid-4-yl)ureaHCID 233290721-Cyclohexylcarbonyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]urea

Product 1

HCID 233290761-Cyclohexylcarbonyl-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-Cyclohexylcarbonyl-3-[1-(2-[1,4-benzodioxan-2-yl]-2-oxoethyl)piperid-4-yl]urea, prepared by reacting 1-cyclohexylcarbonyl-3-(piperid-4-yl)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-658020d779da48ddb1d3b39c93f577b6
Source dataset
uspto-grants-1980_11
Patent number
US04235915

Reaction notes

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