Water → HCID 18365419, compound

HRID 380638Notes

Reaction equation

HRID 380638 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11](=[O:27])[CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([CH2:20]C4C=CC=CC=4)[CH2:16][CH2:15]3)[CH:8]=[CH:7][C:5]=2[N:6]=1.ClC(O[CH:32]([Cl:34])[CH3:33])=O.[OH2:35]>ClCCCl>[CH3:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([C:11](=[O:27])[CH2:12][CH2:13][CH:14]3[CH2:19][CH2:18][N:17]([C:20]([CH:32]([Cl:34])[CH3:33])=[O:35])[CH2:16][CH2:15]3)[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 192442245365-80-4HCID 5213051-Chloroethyl chloroformate

Product 1

HCID 18365419HCID 18365419, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 0.90 g (2.38 mM) of 1-(2-methyl-6-benzthiazolyl)-3-[1-(phenylmethyl)-4-piperidinyl]-1-propanone (Example 27) and 0.33 mL (3.1 mM) of 1-chloroethyl chloroformate was refluxed in 10 mL of 1,2-dichloroethane for 2 hours. The resulting brown solution was cooled to room temperature and diluted with 15 mL of water. This mixture was extracted twice with 20 mL of ethyl acetate. The ethyl acetate extracts were combined, dried (Na2SO4), and evaporated to yield 1.0 g (100%) 1-(2-methyl-6-benzothiazolyl)-3-[(1-chloroethylformyl)-4-piperidinyl]-1-propanone as an oil.

Workup

  1. extractionThis mixture was extracted twice with 20 mL of ethyl acetate
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Sources & evidence

ORD record
ord-4708adf9e56e4145ad92043dc65d8717
Source dataset
uspto-grants-2001_10
Patent number
US06303633B1

Reaction notes

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