HCID 20197294, compound → HCID 20197297, compound

HRID 652449Notes

Reaction equation

HRID 652449 reaction equation
[CH3:1][N:2]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[NH:7][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:15][CH2:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 20197294HCID 20197294, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20197297HCID 20197297, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-[2-[methyl(phenylmethyl)amino]ethyl]-1H-indole-5-carbonitrile (1.3 g) in dry tetrahydrofuran (100 ml) under nitrogen was treated with lithium aluminium hydride (1.0 g) and heated at reflux for 3 h. Excess lithium aluminium hydride was destroyed with wet tetrahydrofuran, the reaction mixture diluted with ethyl acetate (200 ml), filtered and the filtrate evaporated to dryness to give a pale yellow oil which slowly crystallised to give the title compound as a cream solid (1.2 g) m.p. 84°-5°.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customExcess lithium aluminium hydride was destroyed with wet tetrahydrofuran
  4. additionthe reaction mixture diluted with ethyl acetate (200 ml)
  5. filtrationfiltered
  6. customthe filtrate evaporated to dryness
  7. customto give a pale yellow oil which
  8. customslowly crystallised

Sources & evidence

ORD record
ord-25251d2515ca4d799e5e6eb12b6b2752
Source dataset
uspto-grants-1987_06
Patent number
US04672067

Reaction notes

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