Tryptamine → HCID 86601791, compound

HRID 1394250Notes

Reaction equation

HRID 1394250 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][NH2:12])=[CH:2]1.C(N(CC)CC)C.[C:20](Cl)(Cl)=[S:21].[CH3:24][N:25]([CH3:39])[C:26]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:31][CH2:30][CH:29]([NH2:32])[CH2:28][CH2:27]1>C(Cl)(Cl)Cl>[CH3:24][N:25]([CH3:39])[C:26]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:31][CH2:30][CH:29]([NH:32][C:20]([NH:12][CH2:11][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:21])[CH2:28][CH2:27]1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 86601791HCID 86601791, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(1H-Indol-3-yl)-ethylamine (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, N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine 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 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)-ethyl]-thiourea was obtained as a colorless foam in a yield of 185 mg (22%). The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl)-3-[2-(1H-indol-3-yl)-ethyl]-thiourea was obtained as a colorless foam in a yield of 433 mg (52%).

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 two diastereoisomers
  5. customcould be purified by column chromatography [silica gel 60 (50 g); methanol (500 ml)]

Sources & evidence

ORD record
ord-f62c82114299415ca9806cdafd7b59b9
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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