Ammonium Acetate → HCID 58368669, compound

HRID 1192545Notes

Reaction equation

HRID 1192545 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)=[C:4]([C:19](=O)[CH3:20])[CH:3]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:28].[Na+]>CO.C(#N)C>[NH2:28][CH:19]([C:4]1[CH:3]=[C:2]([Cl:1])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[N:12]1[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]1)[CH3:20]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 58368476HCID 58368476, compound

Product 1

HCID 58368669HCID 58368669, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 1-[4-chloro-1-(4-hydroxypiperidin-1-yl)-2-naphthyl]ethanone (74 mg, 0.24 mmol) and ammonium acetate (188 mg, 2.44 mmol) in methanol (1.4 mL) and acetonitrile (1.4 mL) was heated at 65° C. in a sealed tube for 30 minutes. After cooling to room temperature, sodium cyanoborohydride (30.6 mg, 0.487 mmol) was added to the resulting mixture. The reaction was heated at 65° C. for another 4 hours, then cooled to room temperature and quenched with sat. sodium bicarbonate and extracted with dichloromethane. The combined extracts were dried over magnesium sulfate and evaporated to dryness. The crude amine was used directly in the next step. LCMS calculated for C17H22ClN2O (M+H)+: m/z=305.1; Found: 305.1.

Workup

  1. temperatureAfter cooling to room temperature
  2. temperatureThe reaction was heated at 65° C. for another 4 hours
  3. temperaturecooled to room temperature
  4. customquenched with sat. sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined extracts were dried over magnesium sulfate
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-34bf57fdc0b14c34857e3ea27d33b853
Source dataset
uspto-grants-2014_03
Patent number
US08680108B2

Reaction notes

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