Pyrrolidine → HCID 14372579, compound

HRID 1382980Notes

Reaction equation

HRID 1382980 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-4ee0103e92314879b563eb6b4fa541ee
Source dataset
uspto-grants-1989_02
Patent number
US04808624

Reaction notes

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