Oxalic acid dihydrate → N-Benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine oxalate

HRID 447750Notes

Reaction equation

HRID 447750 reaction equation
[CH2:1]([N:8]([CH3:21])[CH2:9][CH2:10][CH:11]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]([CH3:20])[CH:14]=[CH:13][C:12]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([C:25]([OH:27])=[O:26])([OH:24])=[O:23].O.O>CC(C)=O>[C:25]([OH:27])(=[O:26])[C:22]([OH:24])=[O:23].[CH2:1]([N:8]([CH3:21])[CH2:9][CH2:10][CH:11]1[CH2:19][CH2:18][CH2:17][C:16]2[N:15]([CH3:20])[CH:14]=[CH:13][C:12]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 17751624N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine

Product 1

HCID 17751623N-Benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine oxalate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-Benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine oxalate is prepared from a solution of N-benzyl-N-methyl-2-(1-methyl-4,5,6,7-tetrahydro-1H-indol-4-yl)ethanamine in acetone with a slightly excess of HO2CCO2H.2H2O. Slightly pinkish solid. M.p.=123-125° C. 1H NMR (300 MHz, CD3OD): δ 1.37 (m, 1H), 1.65-2.13 (m, 5H), 2.49 (m, 2H), 2.70 (m, 1H), 2.78 (s, 3H), 3.23 (m, 2H), 3.43 (s, 3H), 4.32 (m, 2H), 5.80 (d, J=2.8 Hz, 1H), 6.46 (d, J=2.8 Hz, 1H), 7.48 (s, 5H).

Sources & evidence

ORD record
ord-97851242f3ee4d8a95a0de7f8adeb530
Source dataset
uspto-grants-2013_07
Patent number
US08481567B2

Reaction notes

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