Diisopropyl Ether → Ethyl 4-[[[2-nitrophenyl)-amino]thioxomethyl(phenylmethyl)amino]-1-piperidinecarboxylate

HRID 1534722Notes

Reaction equation

HRID 1534722 reaction equation
[C:1]1([CH2:7][NH:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:20]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N+:29]([O-:31])=[O:30])=[C:21]=[S:22].O(C(C)C)C(C)C>O1CCCC1>[N+:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:20][C:21]([N:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH2:10]1)=[S:22])([O-:31])=[O:30]

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 1376902-Nitrophenyl isothiocyanateHCID 13587975Ethyl 4-[(phenylmethyl)amino]-1-piperidinecarboxylate

Product 1

HCID 13587976Ethyl 4-[[[2-nitrophenyl)-amino]thioxomethyl(phenylmethyl)amino]-1-piperidinecarboxylateYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 42.5 parts of ethyl 4-[(phenylmethyl)amino]-1-piperidinecarboxylate, 30 parts of 1-isothiocyanato-2-nitrobenzene and 270 parts of tetrahydrofuran was stirred for 3 hours at room temperature. 2,2'-Oxybispropane was added and stirring was continued overnight. The precipitated product was filtered off and dried, yielding 48.5 parts (68.5%) of ethyl 4-[[[2-nitrophenyl)-amino]thioxomethyl(phenylmethyl)amino]-1-piperidinecarboxylate; mp. 140° C.; (intermediate 30).

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. filtrationThe precipitated product was filtered off
  4. customdried

Sources & evidence

ORD record
ord-8033db1eff564924968ae10d49439d87
Source dataset
uspto-grants-1992_02
Patent number
USRE033833

Reaction notes

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