Proton sponge → Ethyl 4-[[4-[1-(1-Acetoxypropyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetate Hydrochloride

HRID 993042Notes

Reaction equation

HRID 993042 reaction equation
[ClH:1].Cl.[O:3]=[C:4]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:7][CH2:6][N:5]1[CH2:16][C:17]([C:19]1[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=1)=[O:18].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[C:48](=O)([O:57]C1C=CC([N+]([O-])=O)=CC=1)[O:49][CH:50]([O:53][C:54](=[O:56])[CH3:55])[CH2:51][CH3:52]>CN(C)C=O>[ClH:1].[C:54]([O:53][CH:50]([O:49][C:48]([N:13]1[CH2:12][CH2:11][CH:10]([N:8]2[CH2:7][CH2:6][N:5]([CH2:16][C:17]([C:19]3[CH:31]=[CH:30][C:22]([O:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:21][CH:20]=3)=[O:18])[C:4](=[O:3])[CH2:9]2)[CH2:15][CH2:14]1)=[O:57])[CH2:51][CH3:52])(=[O:56])[CH3:55]

Participants

5

Reactant 3

HCID 88675Proton spongeHCID 18408903HCID 18408903, compoundHCID 18408941HCID 18408941, compound

Product 1

HCID 18408934Ethyl 4-[[4-[1-(1-Acetoxypropyl)oxycarbonylpiperidin-4-yl]-2-oxopiperazin-1-yl]acetyl]phenoxyacetate Hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared in a yield of 115 mg (100%) as a free base from 101 mg of ethyl 4-[[2-oxo-4-(piperidin-4-yl)piperazin-1-yl]acetyl]phenoxyacetate dihydrochloride synthesized according to the method described in WO962503 in the same manner as in Example 8 except that N,N-dimethylformamide, proton sponge and 1-acetoxypropyl 4-nitrophenyl carbonate were used in an amount of 2 ml, 101 mg and 82.8 mg, respectively.

Workup

  1. customsynthesized

Sources & evidence

ORD record
ord-8ede12e261d24b9190bb23a0bf29dd1b
Source dataset
uspto-grants-2002_10
Patent number
US06472397B1

Reaction notes

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