Triethylamine → HCID 178512421, compound

HRID 1600687Notes

Reaction equation

HRID 1600687 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH:15]3[CH2:20][CH2:19][CH:18](N)[CH2:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CS[C:24](=[N:36][C:37]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:38])[NH:25][C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27].C([N:49](CC)CC)C>CN(C)C=O>[C:1]1([N:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH:15]3[CH2:16][CH2:17][CH:18]([N:25]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[C:24]([NH:36][C:37]([O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)=[O:38])=[NH:49])[CH2:19][CH2:20]3)[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 46642131,3-Bis(benzyloxycarbonyl)-2-methylisothioureaHCID 10684726189153-13-7

Product 1

HCID 178512421HCID 178512421, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of trans-N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-cylohexylamine (0.43 g, 1.5 mmol), S-methyl-N,N'-dicarbobenzyloxy isothiourea (Nowak K. and Kania L., Rocz. Chem., 1969;43(11):1953-1960) (0.59 g, 1.65 mmol) and triethylamine (0.18 g, 1.8 mmol) in dimethylformamide (DMF) (50 mL) was stirred at room temperature 3 days. An additional amount of the starting amine (0.075 g, 0.26 mmol) was added, and the reaction mixture was allowed to stand one more day and then evaporated to dryness. The residue was recrystallized from Et2O-hexane to yield trans-N-{4-[2-(4-phenyl-piperazin-1-yl)-ethyl]-cyclohexyl-N, N'-dicarbobenzyloxyguanidine 0.568 g (63%) white solid; mp 136-137° C.

Workup

  1. customevaporated to dryness
  2. customThe residue was recrystallized from Et2O-hexane

Sources & evidence

ORD record
ord-979a161dad2b48d089486caf7afe2d32
Source dataset
uspto-grants-1999_11
Patent number
US05977110

Reaction notes

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