Thiophene → (+/-)-Ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate

HRID 2183578Notes

Reaction equation

HRID 2183578 reaction equation
[CH3:1][O:2][CH:3]1[C:8](=O)[CH2:7][CH2:6][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4]1.[C:15]1([CH2:21][N:22]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:24][CH2:25][NH2:26])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.S1C=CC=C1.[H][H]>CO.[Pt]>[C:28]1([CH2:27][N:22]([CH2:21][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:23][CH2:24][CH2:25][NH:26][CH:8]2[CH2:7][CH2:6][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:4][CH:3]2[O:2][CH3:1])[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

7

Reactant 4

HCID 8030ThiopheneHCID 2724451Ethyl 3-methoxy-4-oxopiperidine-1-carboxylateHCID 11436748(3-Aminopropyl)dibenzylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 54032750(+/-)-Ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylateYield 100.7%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A mixture of ethyl 3-methoxy-4-oxo-1-piperidinecarboxylate (0.248 mol) and N,N-bis(phenylmethyl)-1,3-propanediamine (0.248 mol) in methanol (600 ml) was hydrogenated at 50° C. with platinum on activated carbon (5%, 5 g) as a catalyst in the presence of thiophene (4%, 5 ml). After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated, yielding 109.8 g of (±)-ethyl 4-[[3-[bis-(phenylmethyl)amino]propyl]amino]-3-methoxy-1-piperidinecarboxylate (interm. 1).

Workup

  1. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-95b41691a8ee4f00af14ff9005ff2cc8
Source dataset
uspto-grants-2005_05
Patent number
US06900222B1

Reaction notes

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