Diethyl Ether → 1-(Aminomethyl)cyclohexan-1-ol

HRID 1586171Notes

Reaction equation

HRID 1586171 reaction equation
Cl.[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.C([O-])([O-])=O.[K+].[K+].CCOCC>O>[NH2:2][CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 3084332Cyclohexanol, 1-(aminomethyl)-, hydrochloride (1:1)

Product 1

HCID 776141-(Aminomethyl)cyclohexan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Aminomethyl-1-cyclohexanol hydrochloride (1 g, 6.04 mmol) is dissolved in cold water and then K2CO3 and ether are added. The mixture is stirred, and then the ether layer is separated and the aqueous layer is again extracted with ether. The ether layers are combined, dried over MgSO4 and concentrated to afford 1-aminomethyl-1-cyclohexanol which is mixed with DMSO (3 ml) and 1-ethyl-6-methoxy-1H-pyrazolo[3,4-b]quinoline (0.8 g, 3 mmol). The reaction mixture is stirred at 110° C. overnight, and then is partitioned between water and CH2Cl2. The CH2Cl2 layer is separated, dried, filtered and evaporated. The residue is crystallized from and recrystallized from acetonitrile to afford 0.65 g of 1-ethyl-6-methoxy-N-[(1-hydroxycyclohexyl)methyl]-1H-pyrazolo[3,4-b]quinolin-4-amine, m.p. 201°-203° C.

Workup

  1. customthe ether layer is separated
  2. extractionthe aqueous layer is again extracted with ether
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5f7e3910d2f74aa1ae5293d412ff44fc
Source dataset
uspto-grants-1999_08
Patent number
US05942520

Reaction notes

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