HCID 9860669, compound → 2-Phenethyl-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one

HRID 489526Notes

Reaction equation

[C:1]1([C:7]#[C:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=2[C:16]=34)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pt]=O>[CH2:8]([C:9]1[NH:10][C:11]2[CH:12]=[CH:13][CH:14]=[C:15]3[C:21](=[O:22])[NH:20][CH2:19][CH2:18][C:17]=1[C:16]=23)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 24 °C

Procedure

2-Phenylethynyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one (Compound 17) (37 mg, 0.13 mmol) and platinum oxide (1.5 mg, 0.05 mmol) were suspended in 2 mL MeOH under an argon atmosphere. The flask was flushed with hydrogen gas and the resulting mixture stirred at 24° C. under 1 atmosphere of hydrogen for 20 h. The catalyst was filtered off and the resulting solution concentrated, leaving a pale-yellow crystalline solid. Purification by radial chromatography (5% MeOH in CHCl3) followed by recrystallization (MeOH/CHCl3/hexanes) yielded 2-phenethyl-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 14 mg (37%), as a pale-yellow solid. mp 207-208° C.; 1H NMR (300 MHz, d6-DMSO) δ 2.60 (m, 2H), 2.95 (m, 4H), 3.26 (m, 2H), 7.17 (m, 6H), 7.46 (dd, 1H, J=7.8, 0.6 Hz), 7.61 (dd, 1H, J=7.5, 0.6 Hz), 7.90 (br t, 1H), 11.16 (br s, 1H); MS (FAB, MH+) 291; Anal. (C19H18N2O) C, H, N.

Workup

customThe flask was flushed with hydrogen gas
filtrationThe catalyst was filtered off
concentrationthe resulting solution concentrated
customleaving a pale-yellow crystalline solid
customPurification by radial chromatography (5% MeOH in CHCl3)
customfollowed by recrystallization (MeOH/CHCl3/hexanes)

Sources & evidence

ORD record: ord-5598bfc6210548cab902389c28b979db
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06977298B2

Reaction notes

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