Sodium Sulfate → HCID 21704125, compound

HRID 1595385Notes

Reaction equation

HRID 1595385 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]1[CH2:13][C:12]2([CH2:18][CH2:17][N:16]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[O:11][CH2:10][CH2:9]1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][N:8]1[CH2:13][C:12]2([CH2:14][CH2:15][N:16]([C:19]3[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=3)[CH2:17][CH2:18]2)[O:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 21704118HCID 21704118, compound

Product 1

HCID 21704125HCID 21704125, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride (2 g) was suspended in THF (40 ml) and a solution of 4-(4-methyl-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)benzonitrile (12 g) in THF (100 ml) was added dropwise under ice-cooling. The mixture was stirred at room temperature for 2 hr 40 min and a saturated aqueous sodium sulfate solution was added portionwise under ice-cooling. The precipitated solid was filtrated and washed with chloroform. The chloroform layer was dried over anhydrous sodium sulfate and, after drying, the solvent was evaporated under reduced pressure to give the objective 4-(4-methyl-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)phenylmethylamine (13 g), which was used in the next Starting Material Synthetic Example 185 without purification.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. filtrationThe precipitated solid was filtrated
  4. washwashed with chloroform
  5. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  6. customafter drying
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b0d0888df5044a7a9e0849048031d59f
Source dataset
uspto-grants-2001_09
Patent number
US06288061B1

Reaction notes

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