Dichloromethane → HCID 69115646, compound

HRID 2054167Notes

Reaction equation

HRID 2054167 reaction equation
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C:13]1[CH:14]=[C:15]([CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)[C:16]([CH3:19])=[CH:17][CH:18]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>O1CCCC1>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:2]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])=[CH:14][C:15]=1[CH:20]1[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 60021094HCID 60021094, compound

Product 1

HCID 69115646HCID 69115646, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl chloroformate (95%, 4.52 mL, 30.1 mmol) was added dropwise to a stirred mixture of tert-butyl 4-(3-amino-6-methylphenyl)piperidinecarboxylate (6.99 g, 24.1 mmol) and K2CO3 (3.66 g, 26.4 mmol) in tetrahydrofuran (350 mL) and stirred under nitrogen for 18 h. CH2Cl2 was added to the reaction mixture, washed with NaHCO3 solution (saturated), followed by water, then dried over Na2SO4 and concentrated in vacuo to give an oil. Purification by flash column chromatography (eluent: cyclohexane:EtOAc (87:13)) gave tert-butyl 4-{2-methyl-5-[(phenylmethoxy)carbonylamino]phenyl}piperidinecarboxylate (7.90 g, 77.1% yield) as a white foam. ESMS m/e: 425.0 (M+H)+.

Workup

  1. washwashed with NaHCO3 solution (saturated)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give an oil
  5. customPurification by flash column chromatography (eluent: cyclohexane:EtOAc (87:13))

Sources & evidence

ORD record
ord-9a05e85dae1841db8557fd041f0b83e3
Source dataset
uspto-grants-2008_02
Patent number
US07329656B2

Reaction notes

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