Water → HCID 23452508, compound

HRID 1278061Notes

Reaction equation

HRID 1278061 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:19]=[CH:18][C:11]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][NH:14]2)=[CH:10][CH:9]=1.C(N(CC)CC)C.O>ClCCl>[Cl:7][C:8]1[CH:19]=[CH:18][C:11]([CH2:12][CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:4]([CH:1]2[CH2:3][CH2:2]2)=[O:5])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 5138807HCID 5138807, compound

Product 1

HCID 23452508HCID 23452508, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add (dropwise, at 0° to 8°) 5.2 g of cyclopropanecarboxylic acid chloride in 10 ml of dichloromethane to 10 g of 2-(4-chlorobenzyl)pyrrolidine and 6.2 g of triethylamine. Stir the thus-prepared reaction mixture for a further 2 hours at 0°. Add water thereto. Separate off the organic phase and extract it with dichloromethane. Combine the organic phases and wash them with dilute hydrochloric acid and sodium carbonate solution. Dry the washed material over sodium sulfate. Evaporate off the solvent from the dried material, and then distil the oily residue to obtain the title compound (8.85 g) in the form of oil (b.p. 135° to 137° at 0.005 mm Hg), which solidifies to a crystalline mass of m.p. 62° to 64°.

Workup

  1. customthe thus-prepared reaction mixture for a further 2 hours at 0°
  2. customSeparate off the organic phase
  3. extractionextract it with dichloromethane
  4. washwash them with dilute hydrochloric acid and sodium carbonate solution
  5. dry with materialDry the washed material over sodium sulfate
  6. customEvaporate off the solvent from the dried material
  7. customdistil the oily residue

Sources & evidence

ORD record
ord-b950cad31ef1457782a47f82f19145bf
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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