Piperidine → Ethyl 2-(piperidine-1-carbonyl)-1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate

HRID 1094575Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:12]2[NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=3[C:11]=2[CH2:10][CH:9]([C:20](O)=[O:21])[NH:8][CH:7]=1)=[O:5])[CH3:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>C(Cl)Cl>[N:35]1([C:20]([CH:9]2[NH:8][CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:12]3[NH:13][C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:11]=3[CH2:10]2)=[O:21])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 20 °C

Procedure

To a suspension of 1,2,3,6-tetrahydroazepino[4,5-b]indole-2,5-dicarboxylic acid 5-ethyl ester (45 mg, 0.15 mmol) in DCM (3 mL) was added CDI (27 mg, 1.1 equiv.). After stirring for 1 hour at 20° C., piperidine (23 μL, 1.5 equiv.) was added. The mixture was stirred overnight at 20° C. and a clear solution was obtained. Evaporation of solvent gave a crude product, which was purified by trituration with MeOH to afford the title compound (22 mg); 1H-NMR (CDCl3): δ 10.44 (1H, br s), 7.95 (1H, d), 7.38 (2H, d), 7.05-7.13 (2H, m), 6.69 (1H, d), 4.29 (2H, q), 3.98 (1H, dd), 3.65-3.73 (2H, m), 3.46 (1H, m), 3.31 (1H, m), 2.71 (1H, dd), 1.58-1.76 (6H, m), 1.36 (3H, t); MS (ES): 368 (MH+).

Workup

stirringThe mixture was stirred overnight at 20° C.
customa clear solution was obtained
customEvaporation of solvent
customgave a crude product, which
customwas purified by trituration with MeOH

Sources & evidence

ORD record: ord-0c34965bdd2a4fbdab73ced5d0ad7289
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133992B2

Reaction notes

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