Water → 8-Methyl-1,6,7,8,9,10-hexahydroazepino [4,5-g]indole

HRID 1793807Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]3[CH2:20][CH2:19][N:18]([C:21](OC)=O)[CH2:17][CH2:16][C:14]3=2)[CH:9]=[CH:8]1.O.[OH-].[Na+]>C1COCC1>[CH3:21][N:18]1[CH2:17][CH2:16][C:14]2[C:13](=[CH:12][CH:11]=[C:10]3[C:15]=2[NH:7][CH:8]=[CH:9]3)[CH2:20][CH2:19]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under N2, a flame-dried, 50-mL, two-necked flask was charged with LiAlH4 (0.10 g, equivalent by weight) and THF (3.0 mL) and cooled to 0° C. A solution of methyl 6,7,9,10-tetrahydroazepino[4,5-g]indole-8(1H)-carboxylate (0.105 g, 0.43 mmol) in THF (2.0 mL) was then added and the mixture was stirred at room temperature for 16 hours. Water (0.1 mL) was added slowly, followed by 15% NaOH (0.1 mL) and then water (0.3 mL). The mixture was stirred for 30 min, celite was added and the mixture was filtered through celite and the filtrate concentrated to give 84 mg (98%) of crude product. Crystallization from EtOAc/hexane affords 27 mg of the title product as a beige solid: mp 150–153° C.; 1H NMR (400 MHz, CDCl3) δ 8.09 (br, 1 H), 7.39 (d, J=8 Hz, 1 H), 7.17 (t, J=3 Hz, 1 H), 6.91 (d, J=8 Hz, 6.53 (dd, J=2, 3 Hz, 1 H), 3.10–3.05 (m, 4 H), 2.67–2.62 (m, 4 H), 2.40 (s, 3 H); 13C NMR (100 MHz, CDCl3) δ 135.5, 135.0, 126.5, 123.8, 123.8, 123.6, 121.9, 118.0, 103.1, 57.7, 56.8, 47.6, 36.2, 29.3; HRMS (FAB) calcd for C13H16N2+H 201.1392. found 201.1390.

Workup

stirringThe mixture was stirred for 30 min
additioncelite was added
filtrationthe mixture was filtered through celite
concentrationthe filtrate concentrated
customto give 84 mg (98%) of crude product
customCrystallization from EtOAc/hexane

Sources & evidence

ORD record: ord-18de1c8ffdbb4e7fab89bbefe2407c34
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022694B2

Reaction notes

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