Chloroacetyl chloride → HCID 18946297, compound

HRID 1768948Notes

Reaction equation

HRID 1768948 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[CH:9]=[C:8]([N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)(Cl)Cl>[Cl:23][CH2:24][C:25]([N:15]1[CH2:16][CH2:17][N:12]([C:10]2[CH:9]=[C:8]([N:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[N:7]=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[N:11]=2)[CH2:13][CH2:14]1)=[O:26]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 145852434-(Piperazin-1-yl)-2,6-di(pyrrolidin-1-yl)pyrimidine

Product 1

HCID 18946297HCID 18946297, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

The starting 1-(2-chloroacetyl)-4-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]piperazine was prepared as follows: 1-[2,6-di(1-pyrrolidinyl)-4-pyrimidinyl]piperazine (1.65 g, 5.4 mmol) was dissolved in anhydrous chloroform (30 ml), the solution was cooled to 0°-5° C. and 2-chloroacetyl chloride (0.50 ml, 0.79 g, 7.0 mmol) in anhydrous chloroform (5 ml) was added dropwise under stirring. The mixture was stirred for one hour, concentrated and the residue was dissolved in 100 ml of water. The aqueous solution was made alkaline with conc. NH4OH and stirred for one hour. During this period the separated oil solidified. The solids were collected, washed with icecold water until neutral and dried. In this manner 2.0 g of the desired chloroacetyl compound was obtained, yield: 97.0% mp. 153°-156° C.

Workup

  1. temperaturethe solution was cooled to 0°-5° C.
  2. stirringThe mixture was stirred for one hour
  3. concentrationconcentrated
  4. dissolutionthe residue was dissolved in 100 ml of water
  5. stirringstirred for one hour
  6. waitDuring this period the separated oil solidified
  7. customThe solids were collected
  8. washwashed with icecold water until neutral and
  9. customdried

Sources & evidence

ORD record
ord-8999d8a487e242dcafe8d4189c64edc7
Source dataset
uspto-grants-1995_01
Patent number
US05380724

Reaction notes

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