Tryptamine → HCID 86601797, compound

HRID 1394286Notes

Reaction equation

HRID 1394286 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.C(N(CC)CC)C.[C:20](Cl)(Cl)=[S:21].[NH2:24][CH2:25][CH2:26][CH:27]1[CH2:32][CH2:31][C:30]([N:39]([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:29][CH2:28]1>C(Cl)(Cl)Cl>[CH3:41][N:39]([CH3:40])[C:30]1([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:31][CH2:32][CH:27]([CH2:26][CH2:25][NH:24][C:20]([NH:1][CH2:2][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[NH:6][CH:5]=2)=[S:21])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 69216910HCID 69216910, compound

Product 1

HCID 86601797HCID 86601797, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Tryptamine (320 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, [4-(2-aminoethyl)-1-phenylcyclohexyl]dimethylamine (491 mg, 2 mmole) was added and stirring 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 the expected diastereoisomers and could be purified by column chromatography [silica gel 60 (100 g); MeOH (1000 ml)]. The more polar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea was obtained as a colorless oil in a yield of 330 mg (36%). The more nonpolar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea was obtained as a colorless oil in a yield of 230 mg (25%).

Workup

  1. extractionby extracting the batch with saturated NaHCO3 solution (3×20 ml)
  2. dry with materialThe organic phase was dried with Na2SO4
  3. customevaporated
  4. additiona mixture of the expected diastereoisomers
  5. customcould be purified by column chromatography [silica gel 60 (100 g); MeOH (1000 ml)]

Sources & evidence

ORD record
ord-b7c4512573b94d448b12899abb4d53ec
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

Loading…