Pyrrolidine → HCID 14372579, compound

HRID 620279Notes

Reaction equation

HRID 620279 reaction equation
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([O:19][CH2:20][C:21]([O:23]C)=O)[CH:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>CO>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:20][C:21]([N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:23])[CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 14116888HCID 14116888, compound

Product 1

HCID 14372579HCID 14372579, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-(2-methoxy-2-oxoethoxy)benzamide (1.07 g, 3 mmoles) (prepared in Example 15) in methanol (10 ml) and pyrrolidine (0.952 g, 23 mmoles) was refluxed overnight. The solvent was evaporated and the residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonia (0.5) solvent system. The appropriate fractions were combined, the solvent evaporated and the residue crystallized from 2-propanol and recrystallized from methanol-ether to yield 0.86 g (72%) of the title compound, mp. 160°-162° C.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was chromatographed over deactivated silica
  3. customthe solvent evaporated
  4. customthe residue crystallized from 2-propanol
  5. customrecrystallized from methanol-ether

Sources & evidence

ORD record
ord-4c8a74fb9d18428a87021259cf4f98dc
Source dataset
uspto-grants-1989_04
Patent number
US04820715

Reaction notes

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