Cyclopentylamine → HCID 13089662, compound

HRID 1588232Notes

Reaction equation

HRID 1588232 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>O1CCCC1>[CH:1]1([NH:6][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 2906CyclopentylamineHCID 7748Ethyl bromoacetateHCID 8471Triethylamine

Product 1

HCID 13089662HCID 13089662, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Cyclopentylamine (85.2 g, 1.0 mol) and triethylamine (101.2 g, 1.0 mol) were dissolved in tetrahydrofuran (750 mL) and cooled to 0°-5° C. by means of an ice-water bath. Ethyl bromoacetate (167 g, 1.0 mol) was added dropwise at 0°-5° C. to the solution. After addition the mixture was allowed to warm up to room temperature and then stirred over night at ambient temperature. The precipitated white triethylamine hydrochloride was filtered off and the filtrate concentrated to an oil which was purified over silica gel using hexane/ethyl acetate (8.2) as the eluent. The collected product was dissolved in ether and cooled by means of an ice water bath. Dry hydrogen chloride was bubbled into the solution whereby the HCL salt of the product precipitated. Filtration yielded 138 g of product as a white solid melting at 174°-176° C.

Workup

  1. temperaturecooled to 0°-5° C. by means of an ice-water bath
  2. additionAfter addition the mixture
  3. filtrationThe precipitated white triethylamine hydrochloride was filtered off
  4. concentrationthe filtrate concentrated to an oil which
  5. customwas purified over silica gel
  6. dissolutionThe collected product was dissolved in ether
  7. temperaturecooled by means of an ice water bath
  8. customDry hydrogen chloride was bubbled into the solution whereby the HCL salt of the product
  9. customprecipitated
  10. filtrationFiltration

Sources & evidence

ORD record
ord-c841a07684ef460cb5bd6fb8b9df98ac
Source dataset
uspto-grants-1993_06
Patent number
US05221665

Reaction notes

Loading…