Hydrochloric Acid → Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

HRID 1634254

Reaction equation

HRID 1634254 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([N:17]=[C:18]=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH2:20].Cl.[CH3:22]O>CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][CH3:22])=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 962WaterHCID 2776273Benzyl 4-isocyanatopiperidine-1-carboxylate

Product 1

HCID 18677680Benzyl 4-(methoxycarbonylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 1.0 g (3.9 mmol) of (1-benzyloxycarbonylpiperidin-4-yl)isocyanate from Procedure 1, Step A in 10 mL of methanol was added 5 mg (cat) of DMAP. The reaction was stirred under nitrogen at rt for 24 h and then poured into water containing 2 mL of 2N hydrochloric acid and was extracted twice with ethyl acetate. The organic layers were each washed with a portion of brine, dried over sodium sulfate, combined and concentrated to give 1.4 g of the crude title compound which can be used directly in subsequent reactions.

Workup

  1. extractionwas extracted twice with ethyl acetate
  2. washeach washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e4d00e3aa3214c7ea8248e07f1762dd1
Source dataset
uspto-grants-2003_01
Patent number
US06506777B1

Linked notes

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