1-Bromo-3-chloropropane → N-[1-(3-Chloropropyl)piperidin-4-yl]benzamide

HRID 1531830Notes

Reaction equation

HRID 1531830 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:24][CH2:25][CH2:26][Cl:27]>O1CCCC1>[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:24][CH2:25][CH2:26][Cl:27])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 8471TriethylamineHCID 118120N-4-Piperidylbenzamide

Product 1

HCID 12799158N-[1-(3-Chloropropyl)piperidin-4-yl]benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-benzamidopiperidine (3.2 g; preparation I11), triethylamine (5.67 ml) and 1-bromo-3-chloropropane (2.31 ml) in 150 ml of tetrahydrofuran was refluxed overnight, then concentrated to a small volume and treated with 100 ml of chloroform. The solution was washed with 50 ml of aqueous saturated solution of potassium carbonate, dried over sodium sulfate and concentrated to dryness. The residue (6 g) was purified by silica gel chromatography (eluent chloroform/methanol 9:1) to give, after recrystallization from 20 ml of diethyl ether, 1.63 g of the product, m.p. 145-147° C.

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated to a small volume
  3. additiontreated with 100 ml of chloroform
  4. washThe solution was washed with 50 ml of aqueous saturated solution of potassium carbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness
  7. customThe residue (6 g) was purified by silica gel chromatography (eluent chloroform/methanol 9:1)
  8. customto give
  9. customafter recrystallization from 20 ml of diethyl ether, 1.63 g of the product, m.p. 145-147° C.

Sources & evidence

ORD record
ord-034b44485e0b4a6287cdecd51ac0f502
Source dataset
uspto-grants-2001_03
Patent number
US06200989B1

Reaction notes

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