HCID 178472429, compound → HCID 178525758, compound

HRID 2298971Notes

Reaction equation

HRID 2298971 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[N:14]=2)[CH2:8][CH2:7]1)=[O:5])C>O1CCOCC1.Cl>[NH:14]1[C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=[C:13]1[NH:12][C@H:9]1[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]1

Participants

4

Reactant 1

HCID 178472429HCID 178472429, compound

Product 1

HCID 178525758HCID 178525758, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid ethyl ester (K) (500 mg, 1.7 mmol) in dioxane (4 mL) and HCl (6 N, 8 mL) was heated to 60° C. for 16 h. After cooling, concentration of the reaction mixture gave trans 4-(1H-benzimidazol-2-ylamino)-cyclohexanecarboxylic acid as a white solid (M) (420 mg): 1H NMR (300 MHz, CD3OD) δ7.39 (m, 2 H), 7.28 (m, 2 H), 3.57 (m, 1 H), 2.35 (m, 1 H), 2.18 (br t, 4 H), 1.65-1.40 (m, 4 H); mass spectrum m/z 260 [(M+H)+; calcd for C14H18N3O2: 260].

Workup

  1. temperatureAfter cooling

Sources & evidence

ORD record
ord-c94787deb9004503964a1ee9a42edac3
Source dataset
uspto-grants-2002_12
Patent number
US06495561B2

Reaction notes

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