Aluminium lithium hydride → 1-({2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)methanamine

HRID 2056754Notes

Reaction equation

HRID 2056754 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]3[C:25]4[CH:26]=[CH:27][C:28]([C:30]#[N:31])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@H:14]([CH3:32])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]3[C:25]4[CH:26]=[CH:27][C:28]([CH2:30][NH2:31])=[CH:29][C:24]=4[CH2:23][CH2:22][O:21]3)[C@H:14]([CH3:32])[CH2:13]1)=[CH:7][CH:6]=[CH:5]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 693073181-(2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Product 1

HCID 693065261-({2-[(2R)-4-(6-Fluoro-1-naphthyl)-2-methylpiperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-yl)methanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-{2-[(2R)-4-(6-fluoro-1-naphthyl)-2-methyl-piperazinyl]ethyl}-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.50 g, 1.2 mmol) in dry THF (4 mL) was added lithium aluminium hydride (1M solution in THF) (1.4 mL, 1.4 mmol) and the mixture stirred overnight at room temperature. The reaction was quenched by cautious addition of 2M sodium hydroxide, then extracted into chloroform. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by preparative LC-MS to yield the title compound as a yellow oil. M+H=480.

Workup

  1. customThe reaction was quenched by cautious addition of 2M sodium hydroxide
  2. extractionextracted into chloroform
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by preparative LC-MS

Sources & evidence

ORD record
ord-fb79df0ecfd842799dd09c5f28df9b6b
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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