Water → HCID 61264029, compound

HRID 272809

Reaction equation

HRID 272809 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2([C:21]#[N:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1.O.[OH-].[Na+]>C(OCC)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:21][NH2:22])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 187863664-(3-Methoxyphenyl)oxane-4-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 61264029HCID 61264029, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of LiAlH4 (3.7 g, 96.7 mmol) in diethyl ether (100 mL) cooled at 0° C. was added dropwise a solution of 4-(3-methoxyphenyl)-tetrahydro-pyran-4-carbonitrile (4.2 g, 19.3 mmol) in diethyl ether (100 mL). After being stirred at room temperature for 30 min, the reaction mixture was refluxed for another 15 min. The mixture was cooled to 10° C. and water, sodium hydroxide (15% w/v in water, 0.48 mL) and water again were successively added dropwise. After being stirred for 15 min at room temperature, the mixture was filtered over diatomaceous earth and concentrated. The residue was purified with flash chromatography (DCM/MeOH: 95/5) to provide (4-(3-methoxyphenyl)tetrahydro-pyran-4-yl]methylamine (4 g, 94%).

Workup

  1. temperaturethe reaction mixture was refluxed for another 15 min
  2. temperatureThe mixture was cooled to 10° C.
  3. stirringAfter being stirred for 15 min at room temperature
  4. filtrationthe mixture was filtered over diatomaceous earth
  5. concentrationconcentrated
  6. customThe residue was purified with flash chromatography (DCM/MeOH: 95/5)

Sources & evidence

ORD record
ord-3409e452878b43d78546b9be2173f632
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Linked notes

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