Acetic Acid → HCID 21109896, compound

HRID 1766194Notes

Reaction equation

HRID 1766194 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][N:16]([CH3:26])[CH2:17][CH2:18][CH2:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O>[CH3:26][N:16]([CH3:15])[CH2:17][CH2:18][CH2:19][N:20]1[CH2:21][CH2:22][N:23]([CH:11]2[CH2:12][CH2:13][N:8]([CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:9][CH2:10]2)[CH2:24][CH2:25]1

Participants

9

Reactant 6

HCID 176Acetic AcidHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 192201-Benzyl-4-piperidoneHCID 27362341-[3-(Dimethylamino)propyl]piperazineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21109896HCID 21109896, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 27.8 g (0.15 mol) of 1-(phenylmethyl)-4-piperidinone and 26.5 g (0.15 mol) of 1-(3-dimethylaminopropyl)-piperazine in 500 ml of tetrahydrofuran were added 200 mg of p-toluenesulphonic acid and 13.5 g (0.225 mol) of glacial acetic acid, followed by 47.7 g (0.225 mol) of sodium triacetoxyborohydride, in small batches, and the mixture was stirred overnight at ambient temperature. 100 ml of water were added dropwise while stirring was continued and after 30 minutes sufficient potassium carbonate was added to produce a precipitate that could be filtered off. It was filtered and the filter cake was washed thoroughly with THF and diethylether in succession. The combined filtrates were concentrated by evaporation in vacuo, the residue was purified by column chromatography on 400 g of aluminium oxide (Al2O3—ICN, activity stage 3) using EE/MeOH (95/5 v/v) as eluant. A colourless oil, Rf 0.33 (El O), was obtained in a yield of 35.0 g (68% of theoretical). MS: ESI: (M+H)+=345

Workup

  1. stirringwhile stirring
  2. waitwas continued and after 30 minutes
  3. customto produce a precipitate that
  4. filtrationcould be filtered off
  5. filtrationIt was filtered
  6. washthe filter cake was washed thoroughly with THF and diethylether in succession
  7. concentrationThe combined filtrates were concentrated by evaporation in vacuo
  8. customthe residue was purified by column chromatography on 400 g of aluminium oxide (Al2O3—ICN, activity stage 3)
  9. customA colourless oil, Rf 0.33 (El O), was obtained in a yield of 35.0 g (68% of theoretical)

Sources & evidence

ORD record
ord-46e28487328c4398b6e88fdfa3e07b83
Source dataset
uspto-grants-2007_06
Patent number
US07230001B1

Reaction notes

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