Diethyl Ether → HCID 10025689, compound

HRID 1394263Notes

Reaction equation

HRID 1394263 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 217.8%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (249 mg, 0.63 mmole) was dissolved in acetone (7 ml) and ethyl methyl ketone (15 ml). Chlorotrimethylsilane (121 μl, 0.95 mmole) was added dropwise with stirring at RT. After one hour's stirring, no precipitate had formed. The reaction solution was reduced to approx. 0.5 ml under a vacuum and combined with diethyl ether (10 ml). The mixture was then vigorously stirred at RT for 1 h. An almost colorless precipitate was formed. The solid was filtered out, washed with diethyl ether (3×2.5 ml) and dried under a vacuum. The hydrochloride of the more polar diastereoisomer of 1-(4-dimethylamino-4-phenyl-cyclohexylmethyl)-3-(3-phenyl-propyl)-urea (270 mg, m.p. 100-110° C., 99%; Example 24) was obtained as a grey/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. customAn almost colorless precipitate was formed
  5. filtrationThe solid was filtered out
  6. washwashed with diethyl ether (3×2.5 ml)
  7. customdried under a vacuum

Sources & evidence

ORD record
ord-8460eb927e5c4872ae657b269e279333
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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