Diethyl Ether → HCID 10025688, compound

HRID 346810Notes

Reaction equation

HRID 346810 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.CCOCC>CC(C)=O.CC(=O)CC>[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

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 6397ChlorotrimethylsilaneHCID 10025689HCID 10025689, compound

Product 1

HCID 10025688HCID 10025688, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

In the manner described for Example 27, 255 mg of the polar diastereoisomer of 1-(4-dimethylamino-4-phenylcyclohexylmethyl)-3-(3-phenylpropyl)urea were also obtained (m.p. 159–165° C.). 249 mg (0.63 mmol.) thereof were dissolved in acetone (7 ml) and 2-butanone (15 ml), and chlorotrimethylsilane (121 μl, 0.95 mmol.) was added dropwise at RT, with stirring. After stirring for 1 h, the reaction solution was reduced to about 0.5 ml in vacuo, ether (10 ml) was added thereto, and vigorous stirring was carried out for 1 h at RT. The resulting solid was filtered off with suction, washed with ether (3×2.5 ml) and dried in vacuo. 270 mg of the corresponding hydrochloride of the polar urea were obtained (greyish-white solid, m.p. 100–110° C.).

Workup

  1. customwere also obtained (m.p. 159–165° C.)
  2. stirringAfter stirring for 1 h
  3. additionwas added
  4. stirringvigorous stirring
  5. filtrationThe resulting solid was filtered off with suction
  6. washwashed with ether (3×2.5 ml)
  7. customdried in vacuo

Sources & evidence

ORD record
ord-8adfefd98944466eaddaf8dbdb2b416d
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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