Phosgene → 4-Methylpiperidine-1-carbonyl Chloride

HRID 490307Notes

Reaction equation

HRID 490307 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]>CCCCCC1C=C(O)C2[C@@H]3C=C(C)CC[C@H]3C(C)(C)OC=2C=1.C1(C)C=CC=CC=1>[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 16078TetrahydrocannabinolSolvent

Procedure

9 g (90.75 mmol) of 4-methylpiperidine and 13.9 ml (100 mol) of triethylamine were dissolved in 100 ml of THC and, at −30° C., 54.9 ml (100 mmol) of phosgene in toluene (20 percent) were added, and the mixture was stirred for 2.5 h, during which it warmed to room temperature. The reaction mixture was concentrated, 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-a1f21a1b865e483c9fcdcfde52a01568
Source dataset
uspto-grants-2009_05
Patent number
US07528155B2

Reaction notes

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