Acetic Acid → HCID 58266524, compound

HRID 1888415Notes

Reaction equation

HRID 1888415 reaction equation
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:5]([CH:6]=O)=[C:4]([O:12][CH3:13])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:13][O:12][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[C:8]([O:10][CH3:11])[C:5]=1[CH2:6][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5298942,6-Dimethoxy-4-hydroxybenzaldehydeHCID 5003444Sodium cyanoborohydride

Product 1

HCID 58266524HCID 58266524, compoundYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-hydroxy-2,6-dimethoxybenzaldehyde (0.30 g, 1.65 mmol), piperidine (0.20 mL, 1.98 mmol) and acetic acid (0.47 mL, 8.25 mmol) in methanol (20 mL) was stirred for 20 minutes before addition of sodium cyanoborohydride (0.27 g, 4.30 mmol). The reaction mixture was allowed to stir at ambient temperature for 4 h then loaded onto a 10 g SCX-2 cartridge which was then washed with methanol (30 mL) and then eluted with 2N ammonia in methanol (50 mL). Concentration of the combined basic fractions in vacuo afforded the title compound (220 mg, 53%) as a white solid. 1H NMR (DMSO-D6, 300 MHz): 9.39 (s, 1H), 6.03 (s, 2H), 3.66 (s, 6H), 3.30 (s, 2H), 2.32-2.24 (m, 4H), 1.42-1.35 (m, 4H), 1.34-1.26 (m, 2H). LCMS (Method B): RT=1.90 min, M+H+=252.

Workup

  1. washwas then washed with methanol (30 mL)
  2. washeluted with 2N ammonia in methanol (50 mL)

Sources & evidence

ORD record
ord-63b234bfea1348cd876c41a9f8d0bfd0
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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