Benzylamine → HCID 44160054, compound

HRID 517854Notes

Reaction equation

HRID 517854 reaction equation
[CH3:1][N:2]1[CH2:22][CH2:21][C:5]2[N:6]([CH2:14][CH2:15][C:16](OCC)=[O:17])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:16](=[O:17])[CH2:15][CH2:14][N:6]1[C:7]2[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=2[C:4]2[CH2:3][N:2]([CH3:1])[CH2:22][CH2:21][C:5]1=2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 23932524HCID 23932524, compound

Product 1

HCID 44160054HCID 44160054, compoundYield 29.16%

Conditions

Temperature
100 °C

Procedure

Ethyl 3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanoate (200 mg, 0.66 mmol) was added to benzylamine (2.0 ml, excess) and the reaction mixture was heated at 100° C. for 14 h. After completion of the reaction (monitored by LCMS) it was concentrated and basified with aqueous saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was concentrated to dryness and the crude obtained was purified by silica gel chromatography (Eluent: 10% MeOH in dichloromethane) to get 70 mg (yield: 29.16%) of N-benzyl-3-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)propanamide as a free base. To the free base (40 mg, 0.11 mmol) dissolved in THF (5.0 ml), oxalic acid (13 mg, 0.10 mmol) in THF (5.0 ml) was added slowly, the mixture was stirred at RT for 20 minutes and the solid obtained was filtered, washed with ether and dried to get 35 mg (yield: 71.4%) of N-benzyl-3-(1,2,3,4-tetrahydro-2,8-dimethylpyrid[4,3-b]indol-5-yl)propanamide as oxalate salt. 1H NMR (DMSO) 7.50-7.30 (t, 3H), 7.20-7.10 (m, 3H), 7.0-6.90 (m, 2H), 4.40-4.30 (m, 4H), 4.30-4.20 (t, 2H), 4.0 (s, 2H), 3.10 (m, 2H), 2.90 (s, 3H), 2.60-2.50 (t, 3H), 2.40 (s, 3H).

Workup

  1. customAfter completion of the reaction (monitored by LCMS) it
  2. concentrationwas concentrated
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic layer was concentrated to dryness
  5. customthe crude obtained
  6. customwas purified by silica gel chromatography (Eluent: 10% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-23d3f0dbfc83424e8b72ad5ec4a1cee2
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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