Aluminium lithium hydride → 1h-Indole,3-[2-[4-(4-fluorophenoxy)-1-piperidinyl]ethyl]-

HRID 437570Notes

Reaction equation

HRID 437570 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:16](=O)[C:17]([N:19]2[CH2:24][CH2:23][CH:22]([O:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)=O)=[CH:8]1>O1CCCC1>[F:32][C:29]1[CH:28]=[CH:27][C:26]([O:25][CH:22]2[CH2:21][CH2:20][N:19]([CH2:17][CH2:16][C:9]3[C:10]4[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=4)[NH:7][CH:8]=3)[CH2:24][CH2:23]2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 214287001-(Indol-3-ylglyoxyloyl)-4-(p-fluorophenoxy)piperidine

Product 1

HCID 214286931h-Indole,3-[2-[4-(4-fluorophenoxy)-1-piperidinyl]ethyl]-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

By following the manipulative procedure described in Example 2(d), 2.6 g of lithium aluminum hydride in 80 ml. of tetrahydrofuran and 6.0 g of 1-(indol-3-ylglyoxyloyl)-4-(p-fluorophenoxy)piperidine in 60 ml. of tetrahydrofuran are allowed to react to produce a white solid. The solid is recrystallized from isopropanol, and then from an ethanol and water mixture to give colorless cubes of 3-{2-[4-(p-fluorophenoxy)piperidyl]ethyl}indole, m.p. 109°-111° C.

Workup

  1. customto react
  2. customto produce a white solid
  3. customThe solid is recrystallized from isopropanol

Sources & evidence

ORD record
ord-1806278a9a734bf591afd6bb528c40be
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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