Hydrochloric Acid → HCID 86601798, compound

HRID 1394287Notes

Reaction equation

HRID 1394287 reaction equation
Cl.[CH3:2][N:3]([CH3:33])[C:4]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][NH:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[S:14])[CH2:6][CH2:5]1.C[Si](C)(C)[Cl:36]>CC(CC)=O>[ClH:36].[CH3:33][N:3]([CH3:2])[C:4]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][NH:12][C:13]([NH:15][CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][CH:19]=2)=[S:14])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 86601797HCID 86601797, compound

Product 1

HCID 86601798HCID 86601798, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

In order to produce the hydrochloride, the more nonpolar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea (230 mg, 0.5 mmole) was dissolved in ethyl methyl ketone (5 ml) and combined with trimethylchlorosilane (2.5 ml, 26.8 mmole). The colorless solid which precipitated out was removed by suction filtration after 2 h, washed with ethyl methyl ketone (3×5 ml) and then dried. The more nonpolar diastereoisomer of 1-[2-(4-dimethylamino-4-phenylcyclohexyl)-ethyl]-3-[2-(1H-indol-3-yl)ethyl]thiourea hydrochloride was obtained in this manner as a colorless solid (Example 43, m.p. 130-138° C.) in a yield of 240 mg (99%).

Workup

  1. customThe colorless solid which precipitated out
  2. customwas removed by suction filtration after 2 h
  3. washwashed with ethyl methyl ketone (3×5 ml)
  4. customdried

Sources & evidence

ORD record
ord-f6540c719ca9431785d4db43714af806
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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