Ammonia → HCID 59799433, compound

HRID 1095435Notes

Reaction equation

HRID 1095435 reaction equation
[CH3:1][O:2][C:3]([O:31][CH3:32])([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]OS(C1C=CC(C)=CC=1)(=O)=O.[NH3:33]>CO>[CH3:1][O:2][C:3]([O:31][CH3:32])([C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH2:33]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 59799419HCID 59799419, compound

Product 1

HCID 59799433HCID 59799433, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Toluene-4-sulfonic acid 7,7-dimethoxy-7-[4-(trifluoromethyl)phenyl]heptyl ester (1.82 g, 3.835 mmol) was dissolved in a magnetically stirred solution of 7 M NH3 in methanol (30 ml) and stirred at room temperature for 72 hours. After removal of the solvent in vacuo, the residue was dissolved again in dichloromethane and washed with saturated aqueous NaHCO3. The organic layer was subsequently dried over Na2SO4, filtered and concentrated in vacuo to give crude 7,7-dimethoxy-7-[4-(trifluoromethyl)phenyl]heptylamine (1.43 g) which was not further purified. 1H-NMR (400 MHz, CDCl3) δ 0.88-0.95 (m, 2H), 1.12-1.16 (m, 4H), 1.33-1.38 (m, 2H), 1.83-1.88 (m, 2H), 2.59-2.65 (m, 2H), 3.10-3.26 (m, 8H, including —OMe singlet at 3.14), 7.56 (d, J˜8, 2H), 7.60 (d, J˜8, 2H).

Workup

  1. customAfter removal of the solvent in vacuo
  2. dissolutionthe residue was dissolved again in dichloromethane
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was subsequently dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afb700f238734be4a35168e03fea88f4
Source dataset
uspto-grants-2012_03
Patent number
US08138174B2

Reaction notes

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