4-Aminocyclohexanol → HCID 21101951, compound

HRID 1353423Notes

Reaction equation

HRID 1353423 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.Cl[C:10](OC1C=CC([N+]([O-])=O)=CC=1)=[O:11].C(N(C(C)C)CC)(C)C.[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([N:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1>C(Cl)Cl.CO>[Cl:31][C:32]1[CH:41]=[C:40]2[C:35]([C:36]([N:42]3[CH2:47][CH2:46][N:45]([C:10]([NH:1][CH:2]4[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]4)=[O:11])[CH2:44][CH2:43]3)=[CH:37][CH:38]=[N:39]2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 812934-AminocyclohexanolHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 7383897-Chloro-4-(piperazin-1-yl)quinoline

Product 1

HCID 21101951HCID 21101951, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

As described for example 78, 4-aminocyclohexanol (84 mg, 0.73 mmol), 4-nitrophenyl chloroformate (146 mg, 0.73 mmol), diisopropyl(ethyl)amine (320 mg, 2.4 mmol), and 7-chloro-4-(piperazin-1-yl)quinoline (150 mg, 0.81 mmol) are reacted affording 80 mg of the product after flash chromatography with CH2Cl2-MeOH. 1H NMR (DSMO-d6) 61.17 (m,-4H), 1.74 (m, 4H), 3.38 (m, 2H), 3.56 (br. s, 4H), 3.82 (br., s, 4H), 7.16 (d, 1H), 7.64 (dd, 1H), 1.97 (d, 1H), 8.2 (d, 1H), 8.62 (d, 1H).

Workup

  1. customare reacted

Sources & evidence

ORD record
ord-e74e9d7e0e0847dbb70355eb26b6b113
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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