Ethyl chloroformate → 4-(2,3,4-Trimethoxybenzylthio)-1-cinnamylpiperidine
Reaction equation
C(O)(=O)/C=C/C(O)=O.[CH3:9][O:10][C:11]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[CH:30][C:12]=1[CH2:13][S:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]=[CH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1.C([O-])(=O)/C=C/C([O-])=O.[OH-].[K+].COC1C(OC)=C(OC)C=CC=1CSC1CCN(C(OCC)=O)CC1.ClC(OCC)=O.COC1C(OC)=C(OC)C=CC=1CCl.[Na].CN1CCC(S)CC1>C1C=CC=CC=1.C(O)C>[CH3:9][O:10][C:11]1[C:33]([O:34][CH3:35])=[C:32]([O:36][CH3:37])[CH:31]=[CH:30][C:12]=1[CH2:13][S:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH:22]=[CH:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:17][CH2:16]1Participants
11
Reactant 8
HCID 10928Ethyl chloroformate
HCID 14797Potassium Hydroxide
HCID 97491Toluene, alpha-chloro-2,3,4-trimethoxy-
HCID 5360545Sodium
HCID 5460307Fumarate2×
HCID 141803911-Methylpiperidine-4-thiol
HCID 198909074-(2,3,4-Trimethoxybenzylthio)-1-ethoxycarbonylpiperidine
HCID 678945404-(2,3,4-Trimethoxybenzylthio)-1-cinnamylpiperidine fumarateProduct 1
Reagents, catalysts & solvents 2
Procedure
The 4-(2,3,4-trimethoxybenzylthio)piperidine used as starting material, the fumarate of which melts at 154° C., was prepared by the hydrolysis, using potassium hydroxide and ethanol, of 4-(2,3,4-trimethoxybenzylthio)-1-ethoxycarbonylpiperidine (oil), which was itself prepared by the action of ClCOOC2H5 in benzene on 4-(2,3,4-trimethoxybenzylthio)-1-methylpiperidine (m.p. of the corresponding fumarate: 130° C.), which was itself prepared by the condensation of 2,3,4-trimethoxybenzyl chloride in ethanol with the sodium salt of 1-methyl-4-mercaptopiperidine, b.p./13 : 70°-72° C.
Workup
- custom130° C.
- custom70°-72° C.
Sources & evidence
- ORD record
- ord-723d3b8048ee46d3b6b86ab349d9e5a4
- Source dataset
- uspto-grants-1992_06
- Patent number
- US05126356
Reaction notes
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