Acetic Acid → HCID 9910996, compound

HRID 1532397Notes

Reaction equation

HRID 1532397 reaction equation
C([BH3-])#N.[Na+].[CH2:5]([CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][C:13]1=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27][NH2:28].C(O)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH2:5]([CH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH:13]1[NH:28][CH2:27][C:26]1[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=1[O:24][CH3:23])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 812922-MethoxybenzylamineHCID 5003444Sodium cyanoborohydrideHCID 112648601-benzyl-2-tetralone

Product 1

HCID 9910996HCID 9910996, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (0.46 g, 7.28 mmol) was added to a solution of 1-benzyl-2-tetralone (0.86 g, 3.64 mmol), 2-methoxybenzylamine (0.50 g, 3.64 mmol), and acetic acid (0.22 g, 3.64 mmol) in methanol (10 mL) under nitrogen. After 48 h of stirring, the reaction mixture was concentrated in vacuo to provide a brown oil. Saturated aqueous sodium carbonate solution (25 mL) was added to this residue and the resulting mixture was extracted with chloroform. The chloroform extracts were combined, dried (Na2SO4), and concentrated to provide a brown oil which was purified on flash silica gel (1% methanol-chloroform to 5% methanol-chloroform) to provide 1.0 g of 1-benzyl-2-(2-methoxybenzylamino)tetralin as a brown oil.

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customto provide a brown oil
  3. extractionthe resulting mixture was extracted with chloroform
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto provide a brown oil which
  7. customwas purified on flash silica gel (1% methanol-chloroform to 5% methanol-chloroform)

Sources & evidence

ORD record
ord-d1b690aa90b94551a8d0e1c9cd03594e
Source dataset
uspto-grants-2001_03
Patent number
US06201025B1

Reaction notes

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