Hydrochloric Acid → 1-Amino-N-1H-pyrrol-1-ylcyclopentanecarboxamide Hydrochloride

HRID 22383Notes

Reaction equation

HRID 22383 reaction equation
CC([N:5]([C:9]1([C:14]([NH:16][N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)=[O:15])[CH2:13][CH2:12][CH2:11][CH2:10]1)C(=O)[O-])(C)C.[ClH:22].CCOC(C)=O.CCCCCC.II>C(OCC)(=O)C.C(O)(C)C>[ClH:22].[NH2:5][C:9]1([C:14]([NH:16][N:17]2[CH:21]=[CH:20][CH:19]=[CH:18]2)=[O:15])[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 21226206Ethyl acetate hexaneHCID 867474371,1-dimethylethyl-[1-[(1H-pyrrol-1-ylamino)carbonyl]cyclopentyl]carbamate

Product 1

HCID 199731761-Amino-N-1H-pyrrol-1-ylcyclopentanecarboxamide Hydrochloride

Reagents, catalysts & solvents 1

HCID 22055037Isopropanol ethyl acetateSolvent

Procedure

To a stirred solution consisting of 1,1-dimethylethyl-[1-[(1H-pyrrol-1-ylamino)carbonyl]cyclopentyl]carbamate (2.90 g) in ethyl acetate/isopropanol (30 ml, 3:1) was added excess ethereal HCl. After stirring for 18 hours at room temperature, the reaction appeared complete by TLC (silica gel, 30% EtOAc/hexane, I2 stain). The solid was filtered under nitrogen and recrystallized from ether/methanol to afford 1.40 g of the product, m.p. 218°-220° C.

Workup

  1. filtrationThe solid was filtered under nitrogen
  2. customrecrystallized from ether/methanol

Sources & evidence

ORD record
ord-41f0a9267e774ba1a6c4fde6d1d3b1c9
Source dataset
uspto-grants-1995_06
Patent number
US05428053

Reaction notes

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