Hydrochloric Acid → HCID 69083548, compound

HRID 594377Notes

Reaction equation

HRID 594377 reaction equation
O=[C:2]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][C:13]([O:18][CH3:19])=[CH:12][C:11]=1[O:20][CH3:21])[CH2:3][CH2:4][CH2:5][C:6](OC)=[O:7].C([O-])(=O)C.[NH4+].[BH3-]C#[N:29].[Na+].Cl>CO>[CH3:21][O:20][C:11]1[CH:12]=[C:13]([O:18][CH3:19])[CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH:2]1[NH:29][C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 69082969HCID 69082969, compound

Product 1

HCID 69083548HCID 69083548, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A sealed tube containing a mixture of methyl 5-oxo-5-(2,4,6-trimethoxyphenyl)pentanoate (200 mg; 0.67 mmol), ammonium acetate (520 mg; 6.75 mmol), and NaBH3CN (44 mg; 0.67 mmol) in anh. MeOH (3 ml) was heated to 75° C. for 18 h. After cooling to rt, 2 M aq. HCl was added, and the volatiles were removed under reduced pressure. The aq. solution was extracted with DCM (3×20 ml), and the mixed organic layers were dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded 6-(2,4,6-trimethoxyphenyl)piperidin-2-one as a colorless solid. LC-MS (conditions D): tR=0.86 min.; [M+H]+: 266.84 g/mol.

Workup

  1. additionA sealed tube containing
  2. temperatureAfter cooling to rt
  3. customthe volatiles were removed under reduced pressure
  4. extractionThe aq. solution was extracted with DCM (3×20 ml)
  5. dry with materialthe mixed organic layers were dried over anh. MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customPurification by FC (DCM/MeOH=25/1)

Sources & evidence

ORD record
ord-a31d6dd1e06e4815abfc1366b6b90581
Source dataset
uspto-grants-2016_01
Patent number
US09242970B2

Reaction notes

Loading…