Triethylamine → HCID 86601794, compound

HRID 1394271Notes

Reaction equation

HRID 1394271 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]([NH2:13])[CH3:12])=[CH:2]1.C(N(CC)CC)C.[C:21](Cl)(Cl)=[S:22].[CH3:25][N:26]([CH3:40])[C:27]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH:30]([NH2:33])[CH2:29][CH2:28]1>C(Cl)(Cl)Cl>[CH3:25][N:26]([CH3:40])[C:27]1([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH2:31][CH:30]([NH:33][C:21]([NH:13][CH:11]([CH3:12])[CH2:10][C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)=[S:22])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9287(+-)-alpha-MethyltryptamineHCID 10040ThiophosgeneHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 86601794HCID 86601794, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(1H-indol-3-yl)-1-methyl-ethylamine (349 mg, 2 mmole) was dissolved in dry chloroform (10 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-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea was obtained as a colorless solid in a yield of 256 mg (29%). The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-1-methyl-ethyl]-thiourea was obtained as a colorless solid in a yield of 324 mg (37%).

Workup

  1. additionwas added
  2. extractionby extracting the batch with saturated NaHCO3 solution (3×20 ml)
  3. dry with materialThe organic phase was dried with Na2SO4
  4. customevaporated
  5. additiona mixture of two diastereoisomers
  6. customcould be purified by column chromatography [silica gel 60 (50 g); methanol (500 ml)]

Sources & evidence

ORD record
ord-3c117e6c9a944abaabe3836f3f58418a
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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