Methylamine → HCID 18520090, compound

HRID 1368190Notes

Reaction equation

HRID 1368190 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[CH2:9][N:8]([C:15]([N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([CH2:23][CH2:24][N:25]3C(=O)C4=CC=CC=C4C3=O)[CH2:18]1)=[O:16])[CH2:7][CH2:6]2.CN>>[NH2:25][CH2:24][CH2:23][CH:19]1[CH2:20][CH2:21][CH2:22][N:17]([C:15]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[CH2:9]2)=[O:16])[CH2:18]1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 18520086HCID 18520086, compound

Product 1

HCID 18520090HCID 18520090, compoundYield 95.8%

Procedure

(±)-6,7-Dimethoxy-2-[(3-piperidyl)carbonyl]-1,2,3,4-tetrahydroisoqinoline hydrochloride (3.19 g) was desalted by a customary method, and a conventional alkylation reaction was carried out using an acetonitrile solution (30 ml) of the residue, 2.85 g of N-(2-bromoethyl)phthalimide and 1.55 g of potassium carbonate to give 3.83 g of (±)-6,7-dimethoxy-2-{[3-(2-phthalimidoethyl)piperidyl]carbonyl}-1,2,3,4-tetrahydroisoquinoline. Then, 3.83 g of (±)-6,7-dimethoxy-2-{[3-(2-phthalimidoethyl)piperidyl]carbonyl}-1,2,3,4-tetrahydroisoquinoline was deprotected by a customary method using 45 ml of a methanolic solution containing 40% of methylamine to give 2.67 g of (±)-2-{[3-(2-aminoethyl)piperidyl]carbonyl}-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline as a yellow foamy substance.

Sources & evidence

ORD record
ord-b922099e8d4e4b59a2e8ac1484a48738
Source dataset
uspto-grants-2003_06
Patent number
US06573279B1

Reaction notes

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