Aluminium lithium hydride → 2,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,3-b]indole

HRID 1502631Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[CH:16]=[CH:15][C:14]2[NH:13][C:12]3[CH2:17][CH2:18][CH2:19][N:20]([CH:22]=O)[CH2:21][C:11]=3[C:10]=2[CH:9]=1>C1COCC1>[CH3:22][N:20]1[CH2:19][CH2:18][CH2:17][C:12]2[NH:13][C:14]3[CH:15]=[CH:16][C:8]([CH3:7])=[CH:9][C:10]=3[C:11]=2[CH2:21]1

Participants

Conditions

Temperature: 55 °C

Procedure

To a stirred suspension of lithium aluminum hydride (2 g, 52.63 mmol) in dry THF (150 mL) was added portionwise 9-methyl-3,4,5,6-tetrahydroazepino[4,3-b]indole-2(1H)-carbaldehyde (5.9 g, 25.87 mmol) and the reaction mixture stirred at 55° C. for 2 h. The progress of reaction was monitored by TLC. The reaction mixture was quenched with saturated sodium aqueous sulfate solution at 0° C. and then filtered. The filtrate was dried over anhydrous sodium sulfate and evaporated to dryness to afford the title compound (5.2 g). 1H NMR (DMSO) δ (ppm): 7.12-7.05 (m, 2H), 6.80-6.6.76 (d, 1H), 3.65 (s, 2H), 2.90-2.80 (m, 4H), 2.34 (s, 3H), 2.26 (s, 3H), 1.80-1.72 (m, 2H).

Workup

customThe progress of reaction
customThe reaction mixture was quenched with saturated sodium aqueous sulfate solution at 0° C.
filtrationfiltered
dry with materialThe filtrate was dried over anhydrous sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-8cc6ddf66023426f8f256e37731f86d1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09211287B2

Reaction notes

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