Acetic Acid → HCID 59807063, compound

HRID 1922424Notes

Reaction equation

HRID 1922424 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]1=2.[CH3:12][N:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH3:12][N:13]1[CH2:18][CH2:17][CH:16]([N:1]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]3[CH:8]=[CH:9][CH:10]=[CH:11][C:2]2=3)[CH2:15][CH2:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 740491-Methyl-4-piperidoneHCID 5765032,3,4,5-tetrahydro-1H-1-benzazepineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 59807063HCID 59807063, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 2 (1.0 g, 6.79 mmol), N-methyl-4-piperidone (1.00 mL, 8.15 mmol) and acetic acid (0.96 mL, 16.98 mmol) in dry methanol (10 mL) was treated with NaCNBH3 (0.51 g, 8.15 mmol) at 0° C. The reaction mixture was brought to room temperature and stirred overnight (15 hours). The reaction was quenched with 2N NaOH (100 mL) and extracted with CH2Cl2 (2×25 mL). The combined organic fractions were washed with brine (30 mL), dried (Na2SO4) and concentrated. The crude product was purified by column chromatography (2.0 N NH3 in MeOH:CH2Cl2, 3:97) to give compound 3 (0.82 g, 49.4%) as a yellow oil. 1H-NMR (DMSO-d6) δ 1.55 (m, 4H), 1.74 (m, 4H), 1.96 (td, 2H, J=11.3, 2.6 Hz), 2.15 (s, 3H), 2.66 (m, 2H), 2.78 (m, 2H), 2.93 (m, 2H), 3.17 (m, 1H), 6.74 (t, 1H, J=7.3 Hz), 6.90 (d, 1H, J=8.2 Hz), 7.01 (m, 2H); EI-MS (m/z, %): 244 (M+, 24), 97 (100), 71 (37).

Workup

  1. customwas brought to room temperature
  2. customThe reaction was quenched with 2N NaOH (100 mL)
  3. extractionextracted with CH2Cl2 (2×25 mL)
  4. washThe combined organic fractions were washed with brine (30 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (2.0 N NH3 in MeOH:CH2Cl2, 3:97)

Sources & evidence

ORD record
ord-53a2309137a2410ebbf97265a413eee7
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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