Diethyl Ether → HCID 10025689, compound

HRID 1394262Notes

Reaction equation

HRID 1394262 reaction equation
[CH3:1][N:2]([CH3:29])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[CH2:5][CH2:4]1.[Cl:30][Si](C)(C)C.C(OCC)C>CC(C)=O.CC(CC)=O>[ClH:30].[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[CH2:5][CH2:4]1.[CH3:29][N:2]([CH3:1])[C:3]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:8][CH2:7][CH:6]([CH2:9][NH:10][C:11]([NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:12])[CH2:5][CH2:4]1

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 10025689HCID 10025689, compound

Product 2

HCID 10025688HCID 10025688, compoundHCID 10025689HCID 10025689, compoundYield 218.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexyl-methyl)-3-(3-phenyl-propyl)-urea (310 mg, 0.79 mmole) was dissolved in acetone (5 ml) and ethyl methyl ketone (15 ml). Chlorotrimethylsilane (150 ml, 1.2 mmole) was added dropwise with stirring at RT. After one hour's stirring, no precipitate had formed. The reaction solution was reduced to approx. 1 ml under a vacuum and combined with diethyl ether (10 ml). The mixture was then vigorously stirred at RT for 1 h. A colorless precipitate was formed. The solid was filtered out, washed with diethyl ether (3×3 ml) and dried under a vacuum. The hydrochloride of the more nonpolar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (339 mg, m.p. 85-95° C., 100%; Example 23) was obtained as a colorless solid.

Workup

  1. stirringAfter one hour's stirring
  2. customno precipitate had formed
  3. stirringThe mixture was then vigorously stirred at RT for 1 h
  4. customA colorless precipitate was formed
  5. filtrationThe solid was filtered out
  6. washwashed with diethyl ether (3×3 ml)
  7. customdried under a vacuum

Sources & evidence

ORD record
ord-54bf9535077c4b6ca22b3164282d3e28
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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