N-(2-Piperidylmethyl)-dimethylamine → N,N-Diethyl-2-piperidinemethanamine

HRID 465084Notes

Reaction equation

HRID 465084 reaction equation
CN(C[CH:5]1[CH2:10]C[CH2:8][CH2:7][NH:6]1)C.[C:11](O)(=O)[C@H:12]([C@@H:14]([C:16](O)=O)O)O.[C:21]1([C@@H:27]([N:29]=C=O)C)C=CC=CC=1>C(O)C>[CH2:7]([N:6]([CH2:11][CH:12]1[CH2:14][CH2:16][CH2:21][CH2:27][NH:29]1)[CH2:5][CH3:10])[CH3:8]

Participants

5

Reactant 3

HCID 252484N-(2-Piperidylmethyl)-dimethylamineHCID 439655D-Tartaric acidHCID 2724173(S)-(-)-1-Phenylethyl isocyanate

Product 1

HCID 254287N,N-Diethyl-2-piperidinemethanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound is prepared analogously to Example 52(a) from racemic 2-[(dimethylamino)methyl]piperidine and D-(-)-tartaric acid. The ditartrate melted at 191°-192.5° C. The base, with a boiling point 17 mm Hg 88°-94° C., had a content of (+)-enantiomer determined by reaction with (S)-(-)-1-phenylethylisocyanate and subsequent HPLC investigation, of 98.5%. [α]D20 =+64° (ethanol).

Workup

  1. customwith a boiling point 17 mm Hg 88°-94° C.

Sources & evidence

ORD record
ord-0e6a4e9707a44479b70828a2bf347344
Source dataset
uspto-grants-1985_10
Patent number
US04550107

Reaction notes

Loading…