Aluminium lithium hydride → HCID 10660028, compound

HRID 1095432Notes

Reaction equation

HRID 1095432 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13](=O)[CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[F:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:13][CH2:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 66785340HCID 66785340, compound

Product 1

HCID 10660028HCID 10660028, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

The obtained 1-(5-fluoro-1H-indol-3-yl)-4-(piperazin-1-yl)butan-1-one dihydrochloride (3.20 g) was dissolved in tetrahydrofuran (50 ml) and cooled to 0° C. A solution of LiAlH4 in tetrahydrofuran (60 ml; 1M, ˜53 mmol LiAlH4) was slowly added. Subsequently, the mixture was heated at 80° C. for 20 hours. The excess LiAlH4 was cautiously hydrolyzed and after extractive work-up, 5-fluoro-3-[4-(piperazin-1-yl)butyl]-1H-indole (2.39 g, 98% yield) was obtained. 1H-NMR (400 MHz, DMSO-d6) δ 1.40-1.50 (m, 2H), 1.61 (quintet, J=7, 2H), 2.12-2.35 (m, 7H), 2.60-2.70 (m, 6H), 6.85-6.92 (m, 1H), 7.17 (d, J˜2, 1H), 7.23 (dd, J˜9 and 2, 1H), 7.30 (dd, J˜9 and 4, 1H), 10.85 (br s, 1H).

Workup

  1. temperatureSubsequently, the mixture was heated at 80° C. for 20 hours

Sources & evidence

ORD record
ord-59f9f7794764452b9bfefcccc222e850
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

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