Triethylamine → HCID 68593792, compound

HRID 517874Notes

Reaction equation

HRID 517874 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([NH:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:14].C(N(CC)CC)C>C(O)C>[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([N:8]([CH2:12][C:13]([NH:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[O:14])[NH2:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 23899892-chloro-N-(cyclohexylmethyl)acetamide

Product 1

HCID 68593792HCID 68593792, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

p-Tolylhydrazine hydrochloride (500 mg, 3.16 mmol), 2-chloro-N-(cyclohexylmethyl)acetamide (600 mg, 3.16 mmol), triethylamine (1.31 ml, 9.4 mmol) and ethanol (20 ml) were stirred together to obtain 870 mg of 2-(1-p-tolylhydrazinyl)-N-(cyclohexylmethyl)acetamide. The intermediate (870 mg, 3.15 mmol) and N-methyl-4-piperidone hydrochloride (471 mg, 3.16 mmol) were taken in ethanolic HCl (20 ml) and stirred at RT for 15 min, after which the solvent was removed in vacuo. The reaction mixture obtained was taken in ethanol and heated at 90 deg C. for 14 h. After completion of the reaction (monitored by LCMS), the reaction mixture was concentrated to dryness and basified with aqueous saturated sodium bicarbonate, extracted with ethyl acetate. The organic layer was separated, dried over sodium sulfate and concentrated to obtain the crude product which was purified by silica gel chromatography (Eluent: 10% MeOH in dichloromethane) to yield 70 mg (yield: 6.27%) of N-(cyclohexylmethyl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide. The freebase obtained (70 mg, 0.19 mmol) was dissolve d in THF (10.0 ml), oxalic acid (24 mg, 0.19 mmol) in THF (10.0 ml) was added slowly, the mixture was stirred at RT for 20 min and the solid obtained was filtered, washed with ether and dried to get 70 mg (yield: 80.4%) of N-(cyclohexylmethyl)-2-(1,2,3,4-tetrahydro-2,8-dimethylpyrido[4,3-b]indol-5-yl)acetamide as oxalate salt. 1H NMR (DMSO-D2O) OXALATE SALT 8.3-8.2 (t, 1H), 7.30 (d, 1H), 7.2 (s, 1H), 7.0-6.9 (d, 1H), 4.70 (s, 2H), 4.3 (bs, 2H), 3.80-3.2 (m, 4H), 3.1 (bs, 2H), 2.90 (s, 3H), 2.30 (s, 3H), 1.70-1.50 (m, 5H), 1.40-1.30 (m, 1H), 1.20-1.0 (m, 4H), 0.90-0.70 (m, 1H).

Sources & evidence

ORD record
ord-d5df89d8f64e43a08aecc2e05aa06b8e
Source dataset
uspto-grants-2015_08
Patent number
US09115137B2

Reaction notes

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