Sodium Hydroxide → 9-fluoro-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

HRID 2176148Notes

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[N:11]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C:14](=O)[CH2:13][CH2:12]2.[OH-].[Na+]>S(=O)(=O)(O)O.O1CCOCC1>[F:2][C:3]1[CH:8]=[CH:7][C:6]2[NH:9][C:14]3[CH:15]4[CH2:18][CH2:19][N:11]([CH2:12][C:13]=3[C:5]=2[CH:4]=1)[CH2:17][CH2:16]4

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (4-fluorophenyl)hydrazine hydrochloride (10.67 g, 65.6 mmol; Aldrich) and 1-azabicyclo[3.2.2]nonan-4-one (9.13 g, 65.6 mmol; Example 2A) in 100 mL of 7% sulfuric acid in dioxane was heated to 100° C. for 30 hours. The reaction mixture was basified (˜pH 11) by the addition of 50% aqueous sodium hydroxide then stirred in an ice-bath for 30 minutes. The resulting solid was collected by filtration, washed sequentially with water, hexanes and ether (3×30 mL), and dried to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ 2.06 (m, 4H), 3.03 (m, 3H), 3.23 (m, 2H), 3.65 (s, 1H), 4.18 (s, 2H), 6.77 (ddd, J=2.6, 8.8, 9.6 Hz, 1H), 6.94 (dd, J=2.8, 9.6 Hz, 1H), 7.20 (dd, J=4.0, 8.8 Hz, 1H); MS (ESI) m/z 231 (M+H)+.

Workup

filtrationThe resulting solid was collected by filtration
washwashed sequentially with water, hexanes and ether (3×30 mL)
customdried

Sources & evidence

ORD record: ord-7f9c691ecb7146559a57b5f1cc919e7e
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09063126B2

Reaction notes

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