Diethyl Ether → HCID 13713338, compound

HRID 236402Notes

Reaction equation

HRID 236402 reaction equation
Cl.Cl.[CH3:3][CH:4]([CH3:24])[CH:5]([NH:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)[CH:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[OH:7].[OH-].[Na+].C[CH2:28][O:29]CC.ClC(OC(Cl)(Cl)Cl)=O>C1(C)C=CC=CC=1>[CH3:3][CH:4]([CH:5]1[CH:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[O:7][C:28](=[O:29])[N:14]1[CH2:15][CH2:16][CH2:17][N:18]1[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)[CH3:24]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 10426Diphosgene3×HCID 14798Sodium HydroxideHCID 19791696HCID 19791696, compound

Product 1

HCID 13713338HCID 13713338, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(1RS,2SR)-3-Methyl-1-phenyl-2-(3-piperidinopropylamino)butane-1-ol dihydrochloride (755 mg, 2.00 mmol) was suspended in a 10% aqueons solution of sodium hydroxide (12 ml), followed by addition of ether (28 ml). The mixture was stirred and, when became clear, ice-cooled. A 20% solution of trichloromethyl chloroformate (hereinafter referred to simply as "TCF") in toluene (4.0 ml) was added dropwise over one hour. After completion of the TCF addition, the mixture was stirred at room temperature for 30 minutes. The organic layer was separated, washed once with brine, dried over sodium sulfate and then evaporated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (silica gel: 7 g, solvent: chloroform/methanol=20/1) to obtain 613 mg of the intended compound as pale yellow crystals (yield: 93%).

Workup

  1. temperatureice-cooled
  2. additionwas added dropwise over one hour
  3. stirringthe mixture was stirred at room temperature for 30 minutes
  4. customThe organic layer was separated
  5. washwashed once with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting crude product was purified by silica gel column chromatography (silica gel: 7 g, solvent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-7085d1944a0642e8a8bf98c3f6c2bc58
Source dataset
uspto-grants-1987_02
Patent number
US04644063

Reaction notes

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