N-Methylaniline → Ethyl 4-[[(methylphenylamino)thioxomethyl]amino]-1-piperidinecarboxylate

HRID 1723422Notes

Reaction equation

HRID 1723422 reaction equation
[N:1]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[C:2]=[S:3].[CH3:15][NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.CC1C=CC=CC=1>[CH3:15][N:16]([C:2]([NH:1][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][CH2:5]1)=[S:3])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7515N-MethylanilineHCID 3018454Ethyl 4-isothiocyanatopiperidine-1-carboxylate

Product 1

HCID 14576021Ethyl 4-[[(methylphenylamino)thioxomethyl]amino]-1-piperidinecarboxylateYield 42%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 107 parts of ethyl 4-isothiocyanato-1-piperidinecarboxylate, 53.5 parts of N-methylbenzenamine, 1 part of N,N-dimethyl-4-pyridinamine and 450 parts of methylbenzene was stirred and refluxed overnight. After cooling, the reaction mixture was evaporated. The residue was crystallized from 2,2'-oxybispropane. The product was filtered off and dried, yielding 68 parts (42%) of ethyl 4-[[(methylphenylamino)thioxomethyl]amino]-1-piperidinecarboxylate; mp. 95.2° C. (14).

Workup

  1. temperaturerefluxed overnight
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated
  4. customThe residue was crystallized from 2,2'-oxybispropane
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-fe461f5877394def82cc6640a010b01a
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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