Tryptamine → HCID 10009135, compound

HRID 1394277Notes

Reaction equation

HRID 1394277 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][CH:26]1[CH2:31][CH2:30][C:29]([N:38]([CH3:40])[CH3:39])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:28][CH2:27]1>C(Cl)(Cl)Cl>[CH3:39][N:38]([CH3:40])[C:29]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:30][CH2:31][CH: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])[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 1150TryptamineHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 21082146(4-Aminomethyl-1-phenylcyclohexyl)dimethylamine

Product 1

HCID 10009135HCID 10009135, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
-5 °C

Procedure

Tryptamine (320.4 mg, 2 mmole) was dissolved in dry chloroform (10 ml) and combined with triethylamine (533 μl, 4 mmole). The mixture was cooled to −5° C. Thiophosgene (153.3 μl, 2 mmole) was then added dropwise, resulting in the formation of a precipitate. After a reaction time of 18 h at RT, (4-aminomethyl-1-phenyl-cyclohexyl)-dimethylamine (464.74 mg, 2 mmole) dissolved in chloroform (5 ml) was added. After 20 h stirring at RT, the reaction mixture was clear. Working up was performed by washing the batch with saturated NaHCO3 solution (3×5 ml) and water (5 ml). The organic phase was dried with Na2SO4 and evaporated. The product was a mixture of two diastereoisomers. These were purified and separated by column chromatography [silica gel 60 (70 g); eluent: MeOH/EE 1:1 (1500 ml)]. The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)ethyl]thiourea (266 mg, m.p. 84-87° C., 31%) and also the more polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-[2-(1H-indol-3-yl)ethyl]thiourea (274 mg, m.p. 92-95° C., 32%) were light beige solids.

Workup

  1. customresulting in the formation of a precipitate
  2. additionwas added
  3. washby washing the batch with saturated NaHCO3 solution (3×5 ml) and water (5 ml)
  4. dry with materialThe organic phase was dried with Na2SO4
  5. customevaporated
  6. additiona mixture of two diastereoisomers
  7. customThese were purified
  8. customseparated by column chromatography [silica gel 60 (70 g); eluent: MeOH/EE 1:1 (1500 ml)]

Sources & evidence

ORD record
ord-3275ce07b6a24893b936d87e0bb3b27a
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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