Triethylamine → 1-(4-Dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea
Reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:18](Cl)(Cl)=[S:19].[CH3:22][N:23]([CH3:37])[C:24]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[CH3:22][N:23]([CH3:37])[C:24]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:28][CH:27]([NH:30][C:18]([NH:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[S:19])[CH2:26][CH2:25]1Participants
Procedure
Phenylpropylamine (285 μl, 2 mmole) was dissolved in dry chloroform (15 ml) and combined with triethylamine (555 μl, 4 mmole). Thiophosgene (153 μl, 2 mmole) was added to this mixture. After a reaction time of 16 h, the diastereoisomer mixture of N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine was added and stirring was continued for a further 16 h at RT. Working up was performed by extracting the batch with saturated NaHCO3 solution (3×20 ml). The organic phase was dried with Na2SO4 and evaporated. The product was a mixture of two diastereoisomers and could be purified by column chromatography [silica gel 60 (50 g); methanol (500 ml)]. The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea was obtained as a colorless foam in a yield of 205 mg (25%). The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-(3-phenyl-propyl)-thiourea was obtained as a colorless foam in a yield of 410 mg (50%).
Workup
- additionwas added
- extractionby extracting the batch with saturated NaHCO3 solution (3×20 ml)
- dry with materialThe organic phase was dried with Na2SO4
- customevaporated
- additiona mixture of two diastereoisomers
- customcould be purified by column chromatography [silica gel 60 (50 g); methanol (500 ml)]
Sources & evidence
- ORD record
- ord-d829fc63ae5f4af0ad6b232b246b4b2e
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07348354B2
Reaction notes
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