Phosgene → 4-Methylpiperidine-1-carbonyl Chloride

HRID 2237593Notes

Reaction equation

HRID 2237593 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[C:15](Cl)([Cl:17])=[O:16]>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:15]([Cl:17])=[O:16])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 693814-Methylpiperidine

Product 1

HCID 152215164-Methylpiperidine-1-carbonyl Chloride

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

9 g (90.75 mmol) of 4-methylpiperidine and 13.9 ml (100 mmol) of triethylamine were added at −30° C. to 54.9 ml (100 mmol) of phosgene in toluene (20 percent) and 100 ml of THF and, after stirring for 2.5 h, the reaction mixture was allowed to warm to room temperature. The reaction mixture was concentrated and the residue was mixed with methylene chloride and filtered off, and the filtrate was concentrated. The crude product (12.7 g) was reacted without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe residue was mixed with methylene chloride
  3. filtrationfiltered off
  4. concentrationthe filtrate was concentrated
  5. customThe crude product (12.7 g) was reacted without further purification

Sources & evidence

ORD record
ord-36f3e7ea07e141249f24105634e79451
Source dataset
uspto-grants-2010_05
Patent number
US07718669B2

Reaction notes

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