Aluminium lithium hydride → HCID 58842520, compound

HRID 1270437Notes

Reaction equation

HRID 1270437 reaction equation
[C:1]1([NH:11][C:12]([C:14]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([NH:11][CH2:12][C:14]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 58842701HCID 58842701, compound

Product 1

HCID 58842520HCID 58842520, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-phenyl-cyclohexanecarboxylic acid isoquinolin-1-ylamide (0.117 g; 0.35 mmol) in tetrahydrofuran (10 mL) was cooled to 0° C. and treated with lithium aluminum hydride (0.040 g; 1.05 mmol). The reaction mixture was allowed to slowly warm to room temperature. After 18 h at room temperature additional lithium aluminum hydride was added (0.04 g; 1.05 mmol) and the reaction mixture was heated at 40° C. for 2 h. The reaction mixture was cooled back to 0° C. and carefully quenched by the dropwise addition of water. The tetrahydrofuran was removed by evaporation and the crude residue was diluted with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated, washed with saturated aqueous sodium chloride, dried (magnesium sulfate), filtered and concentrated. Column chromatography on silicia gel using 7:3 hexane:ethyl acetate as the eluent gave 0.042 g of isoquinolin-1-yl-(1-phenyl-cyclohexylmethyl)-amine as a light yellow oil. LCMS m/z=317.2 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ (ppm) 7.96 (1H, d, J=6.0 Hz), 7.54–7.26 (9H, m), 6.61 (1H, d, J=6.0 Hz), 4.80 (1H, broad S), 3.76 (2H, d, J=5.4 hz), 2.26–2.20 (2H, m), 1.84–1.77 (2H, m), 1.66–1.61 (2H, m), 1.55–1.43 (4H, m); 13C NMR (CDCl3, 75 MHz) 155.4, 144.9, 141.4, 137.1, 129.5, 128.9 (two carbons), 127.1, 127.0 (two carbons), 126.4, 125.8, 121.0, 118.1, 110.5, 52.2, 42.6, 34.3 (two carbons), 26.6, 22.2 (two carbons).

Workup

  1. temperaturethe reaction mixture was heated at 40° C. for 2 h
  2. temperatureThe reaction mixture was cooled back to 0° C.
  3. customcarefully quenched by the dropwise addition of water
  4. customThe tetrahydrofuran was removed by evaporation
  5. additionthe crude residue was diluted with ethyl acetate and saturated aqueous sodium bicarbonate
  6. customThe organic layer was separated
  7. washwashed with saturated aqueous sodium chloride
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-9eff258222854469b0063873de0b2d81
Source dataset
uspto-grants-2007_04
Patent number
US07202253B2

Reaction notes

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