Diethyl Carbonate → HCID 14181057, compound

HRID 1638564Notes

Reaction equation

HRID 1638564 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:9](=O)([O:13]CC)[O:10][CH2:11][CH3:12]>CN(C)C1C=CN=CC=1.CO>[CH2:11]([O:10][C:9]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)=[O:13])[CH3:12]

Participants

5

Reactant 2

HCID 7766Diethyl CarbonateHCID 235274-(Aminomethyl)piperidine

Product 1

HCID 14181057HCID 14181057, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

The solution of 1.70 g (9.0 mmol) of 4-(ethoxycarbonylamino-methyl)-piperidine (obtained from 4-aminomethyl-piperidine and diethyl carbonate in the presence of 4-dimethylaminopyridine) in 18 ml of methanol was treated with 9.0 ml (9.0 mmol) of 1N methanolic hydrochloric acid. After addition of 0.53 g (3.0 mmol) of 8-methoxy-2-tetralone, the mixture was stirred for a further 5 minutes. 0.20 g (3.3 mmol) of sodium cyanoborohydride was then added and the mixture was stirred for 15 hours at room temperature, followed by standing for 18 days at about +4° C.

Sources & evidence

ORD record
ord-f09a7758e3dd4d519c811f82580db8da
Source dataset
uspto-grants-1989_11
Patent number
US04880802

Reaction notes

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