Acetic Acid → HCID 57949337, compound

HRID 2427546Notes

Reaction equation

HRID 2427546 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:24][CH:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:23])([F:22])[F:21])=[CH:15][CH:14]=1)[CH2:7]2.[C:31](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO.ClCCl>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:24][CH:25]2[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]2)[CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([F:22])([F:23])[F:21])=[CH:15][CH:14]=1)[CH2:7]2

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 57949296HCID 57949296, compound

Product 1

HCID 57949337HCID 57949337, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

7-Methyl-5-piperidin-4-ylmethyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (50.0 mg, 0.124 mmol) was dissolved in methanol (0.2 mL) and acetic acid (0.2 mL) and 37% formaldehyde (0.2 mL) was added at room temperature. The mixture was stirred for ten minutes and sodium cyanoborohydride (1M in THF, 0.2 mL, 0.20 mmol) was added and the mixture was allowed to stir overnight at room temperature. The reaction was diluted with dichloromethane, washed with sodium bicarbonate (sat) and brine dried over sodium sulphate, filtered and concentrated. Column chromatography provided the title compound as an off white foam (23.8 mg, 44%). 1H NMR (300 MHz, CDCl3): δ 7.37 (d, 2H), 7.21 (d, 2H), 6.99 (d, 2H), 4.77 (s, 2H), 4.22 (s, 2H), 2.91 (d, 1H), 2.77 (m, 4H), 2.58 (d, 2H), 2.30 (m, 3H), 1.99 (m, 1H), 1.67-1.27 (m, 6H).

Workup

  1. stirringto stir overnight at room temperature
  2. washwashed with sodium bicarbonate (sat) and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3b82290669c840819eea4530c22b1bb4
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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