Aluminium lithium hydride → HCID 58689760, compound

HRID 1911764Notes

Reaction equation

HRID 1911764 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 mixture 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 mixture 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-6daf682a28fc4798a91b1aebbc9c8f95
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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