1-Chloroethyl chloroformate → HCID 66594600, compound

HRID 1091374Notes

Reaction equation

HRID 1091374 reaction equation
[Cl:1]C(OC(Cl)C)=O.[C:8]([N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C@@H:24]3[O:29][CH2:28][CH2:27][N:26](CC4C=CC=CC=4)[CH2:25]3)=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)(=[O:10])[CH3:9]>ClC(Cl)C>[ClH:1].[C:8]([N:11]1[CH2:12][CH2:13][CH:14]([O:17][C:18]2[CH:19]=[CH:20][C:21]([C@@H:24]3[O:29][CH2:28][CH2:27][NH:26][CH2:25]3)=[CH:22][CH:23]=2)[CH2:15][CH2:16]1)(=[O:10])[CH3:9]

Participants

4

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 66594811HCID 66594811, compound

Product 1

HCID 66594600HCID 66594600, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

1-Chloroethyl chloroformate (0.92 g, 6.43 mmol) was added to a solution of (2S)-2-(4-(1-acetylpiperidin-4-yloxy)phenyl)-4-benzylmorpholine (1.68 g, 4.26 mmol) in dichloroethane (30 ml). The reaction mixture was stirred vigorously at room temperature for 10 hours. The solvent was evaporated under reduced pressure and methanol (40 ml) was added to the residue. The mixture was heated at 80° C. for one hour, and then the solvent was evaporated under reduced pressure to give a white solid, which was recrystallized from ethanol to afford (2S)-2-(4-(1-acetylpiperidin-4-yloxy)phenyl)morpholine hydrochloride (1.3 g, 100%) as white crystals.

Workup

  1. customThe solvent was evaporated under reduced pressure and methanol (40 ml)
  2. additionwas added to the residue
  3. temperatureThe mixture was heated at 80° C. for one hour
  4. customthe solvent was evaporated under reduced pressure
  5. customto give a white solid, which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-efe3eb0b4f974ec989ff738bbff74055
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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