Pyridine → 4-Methoxypiperidine-1-carbonyl chloride

HRID 225424Notes

Reaction equation

HRID 225424 reaction equation
ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.Cl.[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.N1C=CC=CC=1>ClCCl>[CH3:14][O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:7]([Cl:10])=[O:6])[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 94429TriphosgeneHCID 115428134-Methoxypiperidine hydrochloride

Product 1

HCID 753563324-Methoxypiperidine-1-carbonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of triphosgene (7.4 g, 0.025 mmol) in dichloromethane (200 ml) at ice bath was added dropwise a solution of 4-methoxy-piperidine hydrochloride salt (10 g, 0.066 mmol) and pyridine (10.9 g, 0.139 mmol) in dichloromethane (100 ml). The mixture was stirred over night and filtered through a silica pad, eluting with dichloromethane and evaporated. After trituration with diisopropyl ether, the mixture was used without purification.

Workup

  1. filtrationfiltered through a silica pad
  2. washeluting with dichloromethane
  3. customevaporated
  4. customAfter trituration with diisopropyl ether, the mixture was used without purification

Sources & evidence

ORD record
ord-881f6fc899104a928d52a0b649bc775f
Source dataset
uspto-grants-2009_07
Patent number
US07557101B2

Reaction notes

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