1-Chloro-4-(chloromethyl)benzene → HCID 783165, compound

HRID 444210Notes

Reaction equation

HRID 444210 reaction equation
[C:1]([N:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2].[Cl:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17]Cl)=[CH:15][CH:14]=1>C(O)C>[C:1]([N:6]1[CH2:11][CH2:10][N:9]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([Cl:12])=[CH:14][CH:15]=2)[CH2:8][CH2:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 84311-Piperazinecarboxylic acid, ethyl ester

Product 1

HCID 783165HCID 783165, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-carboethoxypiperazine (25 g; 0.157 mole), 4-chlorobenzyl chloride (26 g; 0.162 mole) and ethanol (250 ml) was gently refluxed for 5 hours and the solvent removed in vacuo. The resulting oil crystallised on cooling to give the hydrochloride of the title compound. Recrystallisation from ethanol gave 29 g (58%) of material of m.p. 208°-210°. (Found; C, 52.70; H, 6.41; N, 8.62; Cl, 21.51; C14H19ClN2O2HCl requires; C, 52.67; H, 6.31; N, 8.78; Cl, 22.20%).

Workup

  1. temperaturewas gently refluxed for 5 hours
  2. customthe solvent removed in vacuo
  3. customThe resulting oil crystallised
  4. temperatureon cooling

Sources & evidence

ORD record
ord-1b23b9ade99441a89adad6fbc4917bc0
Source dataset
uspto-grants-1981_04
Patent number
US04263299

Reaction notes

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