Aluminium lithium hydride → 3-{2-[4-(3-Methylphenoxy)piperidin-1-yl]ethyl}-1H-indole

HRID 437558Notes

Reaction equation

HRID 437558 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=O)[C:11]([N:13]2[CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[CH2:15][CH2:14]2)=O)=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:22]1([CH3:26])[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH:16]2[CH2:15][CH2:14][N:13]([CH2:11][CH2:10][C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:18][CH2:17]2)[CH:21]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 214287061-(1H-Indol-3-yl)-2-[4-(3-methylphenoxy)-1-piperidinyl]-1,2-ethanedione

Product 1

HCID 214287243-{2-[4-(3-Methylphenoxy)piperidin-1-yl]ethyl}-1H-indole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 10.0 of 1-(indol-3ylglyoxyloyl)-4-(m-tolyloxy)piperidine in 205 ml. of tetrahydrofuran is added dropwise to a stirred suspension of 4.8 g of lithium aluminum hydride in 140 ml. of tetrahydrofuran. After the addition is complete, the mixture is stirred and refluxed for 3 hours under nitrogen, cooled, and the excess hydride is carefully destroyed with water. The inorganic precipitate is filtered off and washed with tetrahydrofuran. The filtrate is concentrated, under reduced pressure, to a clear oil which crystallizes to a white solid. The solid is recrystallized from acetonitrile to give white needles of 3-{2-[4-(m-tolyloxy)piperidyl]ethyl}indole, m.p. 145°-146° C.

Workup

  1. additionAfter the addition
  2. temperaturerefluxed for 3 hours under nitrogen
  3. temperaturecooled
  4. customthe excess hydride is carefully destroyed with water
  5. filtrationThe inorganic precipitate is filtered off
  6. washwashed with tetrahydrofuran
  7. concentrationThe filtrate is concentrated, under reduced pressure, to a clear oil which
  8. customcrystallizes to a white solid
  9. customThe solid is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-0cd63ac791b341b497b8c7226deb07d5
Source dataset
uspto-grants-1977_06
Patent number
US04031221

Reaction notes

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