1-Bromo-3-chloropropane → HCID 21250989, compound

HRID 1531832Notes

Reaction equation

HRID 1531832 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2].C(N(CC)CC)C.Br[CH2:19][CH2:20][CH2:21][Cl:22]>O1CCCC1>[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:19][CH2:20][CH2:21][Cl:22])[CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropane2×HCID 8471Triethylamine2×HCID 14451564-Acetamidopiperidine

Product 1

HCID 21250989HCID 21250989, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-acetamidopiperidine (1.4 g; preparation 14), triethylamine (3.56 ml) and 1-bromo-3-chloropropane (1.45 ml) in 50 ml of tetrahydrofuran was refluxed overnight, then an additional 3.5 ml of triethylamine and 1.45 ml of 1-bromo-3-chloropropane were added. After a further 3 hours at reflux, the mixture was concentrated to a small volume, treated with chloroform and washed with aqueous saturated solution of potassium carbonate. The organic phase was dried over sodium sulfate, concentrated to dryness and the residue (2.3 g of a green oil) was purified by silica gel chromatography (eluent chloroform/methanol 9:1) to give 0.67 g of the product, m.p. 74-77° C.

Workup

  1. temperaturewas refluxed overnight
  2. temperatureAfter a further 3 hours at reflux
  3. concentrationthe mixture was concentrated to a small volume
  4. additiontreated with chloroform
  5. washwashed with aqueous saturated solution of potassium carbonate
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customthe residue (2.3 g of a green oil) was purified by silica gel chromatography (eluent chloroform/methanol 9:1)

Sources & evidence

ORD record
ord-e397f515b1204a18ba1ab6f10a43f745
Source dataset
uspto-grants-2001_03
Patent number
US06200989B1

Reaction notes

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