Dichloromethane → Dimethyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

HRID 61474Notes

Reaction equation

HRID 61474 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][NH:7][C@H:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)=[O:10])[C@@H:5]([C:23]([O:25][CH3:26])=[O:24])[CH2:4]1.C(Cl)Cl.Cl[C:31]([O:33][CH3:34])=[O:32]>CN(C)C1C=CN=CC=1>[CH3:1][O:2][C@@H:3]1[CH2:8][N:7]([C:31]([O:33][CH3:34])=[O:32])[C@H:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:12]2)=[O:10])[C@@H:5]([C:23]([O:25][CH3:26])=[O:24])[CH2:4]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 67304478Methyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 67304314Dimethyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a mixture of methyl(2S,3S,5S)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate (0.0233 g, 0.0000645 mol) and 4-dimethylaminopyridine (0.0118 g, 0.0000967 mol) in methylene chloride (1.00 mL, 0.0156 mol) was added methyl chloroformate (0.00648 mL, 0.0000838 mol). The reaction was stirred at rt overnight. After quenched with aq. sodium bicaronate, the reaction was extracted with ethyl acetate. The combined organic layers were washed with brine, dried, concentrated to dry. The resulting residue was used directly in next step. MS (ESI): (M+H)+=420.2.

Workup

  1. customAfter quenched with aq. sodium bicaronate
  2. extractionthe reaction was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry

Sources & evidence

ORD record
ord-11bc39fb4e5d41da9dd49d4b36931e4f
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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