Aluminium lithium hydride → HCID 58689760, compound

HRID 577794Notes

Reaction equation

HRID 577794 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH:7]1([CH2:12][N:13]([CH2:26][CH3:27])[C:14]2[C:23]([C:24]#[N:25])=[CH:22][C:21]3[CH2:20][CH2:19][CH2:18][CH2:17][C:16]=3[N:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8]1>C1COCC1>[NH2:25][CH2:24][C:23]1[C:14]([N:13]([CH2:12][CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:26][CH3:27])=[N:15][C:16]2[CH2:17][CH2:18][CH2:19][CH2:20][C:21]=2[CH:22]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 574868292-(Cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

Product 1

HCID 58689760HCID 58689760, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LAH (0.600 g, 16 mmol) in THF (15 mL), was added a solution of 2-(cyclopentylmethyl-ethyl-amino)-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.300 g, 1.06 mmol) in dry THF. This reaction mixure was gently refluxed for 14 h. The unreacted LAH was then quenched with a saturated solution of sodium sulfate, and the residue was filtered off and washed with diethyl ether. The washings were collected, dried over sodium sulfate, and the solvent was evaporated to provide (3-aminomethyl-5,6,7,8-tetrahydro-quinoline-2-yl)-cyclopentylmethyl-ethylamine (0.2 g), yield: 65%.

Workup

  1. temperatureThis reaction mixure was gently refluxed for 14 h
  2. customThe unreacted LAH was then quenched with a saturated solution of sodium sulfate
  3. filtrationthe residue was filtered off
  4. washwashed with diethyl ether
  5. customThe washings were collected
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-427fc894f67e46bc957c8c00f5918243
Source dataset
uspto-grants-2015_05
Patent number
US09040558B2

Reaction notes

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