Ammonia → 1-(4-Hydroxyphenyl)cyclopentane-1-carboxamide

HRID 1955650Notes

Reaction equation

HRID 1955650 reaction equation
O[N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2N=N1.Cl.C(N=C=NC[CH2:18][CH2:19]N(C)C)C.CN1CC[O:27]CC1.N.[O:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[OH:31][C:35]1[CH:19]=[CH:18][C:32]([C:7]2([C:6]([NH2:2])=[O:27])[CH2:8][CH2:9][CH2:10][CH2:5]2)=[CH:33][CH:34]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 79724-MethylmorpholineHCID 8028TetrahydrofuranHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 188010961-(4-Hydroxyphenyl)cyclopentane-1-carboxamide

Procedure

1-Hydroxybenzotriazole (3.68 g, Aldrich), 1-Ethyl-3-(3-Dimethylaminopropyl)-carbodiimide hydrochloride (5.28 g Sigma) and N-Methylmorpholine (2.78 g, Aldrich) were added, under nitrogen, to a stirred solution of the product from Example 4(a) (5.0 g) in dry tetrahydrofuran (THF). The mixture was stirred at RT for four hours, then slowly added to liquid ammonia (excess) at -60° C. After one hour, the mixture was warmed to RT and stirred overnight.

Workup

  1. waitAfter one hour
  2. temperaturethe mixture was warmed to RT
  3. stirringstirred overnight

Sources & evidence

ORD record
ord-f2b4f400ca4d42d688c0ec9313a4326f
Source dataset
uspto-grants-1998_07
Patent number
US05776951

Reaction notes

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