Water → HCID 54204989, compound

HRID 1531829Notes

Reaction equation

HRID 1531829 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][Cl:11])[CH2:4][CH2:3]1.[C:12](=[O:15])([O-])[O-].[Na+].[Na+].[C:18]1([CH3:27])[C:19](C(Cl)=O)=[CH:20][CH:21]=[CH:22][CH:23]=1.O>C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[CH3:27][C:18]1[CH:19]=[CH:20][C:21]([C:12]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][Cl:11])[CH2:4][CH2:3]2)=[O:15])=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 702762-Methylbenzoyl chlorideHCID 21250994HCID 21250994, compound

Product 1

HCID 54204989HCID 54204989, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 3-(4-aminopiperidin-1-yl)-1-chloropropane (1g; preparation 9), sodium carbonate (0.42 g) and toluoyl chloride (0.58 ml) in 20 ml of ethyl acetate and 20 ml of saturated aqueous sodium bicarbonate solution was stirred at room temperature for 3 hour, then poured into 100 ml of water. The organic phase was separated, dried over sodium sulfate and concentrated to dryness. The residue (1.4 g) was crystallized from 20 ml of hexane and the collected solid dried under vacuum at 50° C. to give 1.05 g of the product, m.p. 150-152° C.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe residue (1.4 g) was crystallized from 20 ml of hexane
  5. customthe collected solid dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-951be12cde22400aaf3cc4d093a724d1
Source dataset
uspto-grants-2001_03
Patent number
US06200989B1

Reaction notes

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