1-Bromo-3-chloropropane → HCID 21250986, compound

HRID 1531833Notes

Reaction equation

HRID 1531833 reaction equation
[C:1]([NH:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)(=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].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])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropane2×HCID 8471Triethylamine2×HCID 21250996HCID 21250996, compound

Product 1

HCID 21250986HCID 21250986, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-heptanoylaminopiperidine (7.49 g; preparation 16), triethylamine (9.79 ml) and 1-bromo-3-chloropropane (5.38 ml) in 200 ml of dry tetrahydrofuran was refluxed for 4 hours, then a further 9.79 ml of triethylamine and 5.38 ml of 1-bromo-3-chloropropane were added. The reaction mixture was refluxed overnight, then concentrated to dryness, treated with 100 ml of saturated aqueous potassium carbonate solution and extracted with ethyl acetate (2×100 ml). The organic extracts were pooled, dried over sodium sulfate and concentrated to dryness to give 15 g of an oil which was purified by silica gel chromatography (eluent chloroformlmethanol 9:1) to give, after crystallization from 30 ml of hexane, 6.12 g of the product, m.p. 68-70° C.

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureThe reaction mixture was refluxed overnight
  3. concentrationconcentrated to dryness
  4. additiontreated with 100 ml of saturated aqueous potassium carbonate solution
  5. extractionextracted with ethyl acetate (2×100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-4372529ec7ea4bb4b827284e06603fb8
Source dataset
uspto-grants-2001_03
Patent number
US06200989B1

Reaction notes

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