Hydrochloric Acid → HCID 53414028, compound

HRID 361827Notes

Reaction equation

HRID 361827 reaction equation
Cl.CN.[OH-].[K+].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[CH:15]([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:21]([BH3-])#[N:22].[Na+].Cl>CO>[CH2:6]([N:13]1[CH2:18][CH2:17][CH:16]([NH:22][CH3:21])[CH:15]([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 5609651-Benzyl-3-methyl-4-piperidoneHCID 5003444Sodium cyanoborohydrideHCID 6364545Methylamine hydrochloride

Product 1

HCID 53414028HCID 53414028, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methylamine hydrochloride (1.40 g) in methanol (30 ml) at 0° under nitrogen is treated with potassium hydroxide pellets (331 mg) followed by the racemic 1-benzyl-3-methyl-4-piperidone (3.00 g) and is stirred at 0° for 20 min. Then sodium cyanoborohydride (371 mg) is added, and the reaction mixture is warmed to 20°-25° and stirred at 20°-25° for 18 hrs. The mixture is then adjusted to pH 2.5 with 3M aqueous hydrochloric acid, concentrated under reduced pressure, diluted with water (40 ml), adjusted to pH 12 with potassium hydroxide pellets, saturated with sodium chloride, and extracted with methylene chloride (3×40 ml). The combined organic phase is dried over sodium sulfate and concentrated under reduced pressure to give the 1-benzyl-3-methyl-4-(methylamino)piperidine intermediate as a diastereomeric mixture.

Workup

  1. temperaturethe reaction mixture is warmed to 20°-25°
  2. stirringstirred at 20°-25° for 18 hrs
  3. concentrationconcentrated under reduced pressure
  4. additiondiluted with water (40 ml)
  5. extractionextracted with methylene chloride (3×40 ml)
  6. dry with materialThe combined organic phase is dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d07b75c94cb34c1b9ab9a04ad8ec44aa
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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