Dicyclohexylcarbodiimide → 4-Diethylaminobutyrate dihydrochloride

HRID 1657463Notes

Reaction equation

HRID 1657463 reaction equation
O.C(C1C=C(O)C2C(C3CCN(CC4C=CC5C(=CC=CC=5)C=4)CC=3)CC(C)(C)OC=2C=1)CCCC.[ClH:37].[CH2:38]([N:40]([CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45])[CH3:39].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[ClH:37].[ClH:37].[CH2:47]([N:40]([CH2:38][CH3:39])[CH2:41][CH2:42][CH2:43][C:44]([OH:46])=[O:45])[CH3:48]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 137955394-(Diethylamino)butanoic acid hydrochlorideHCID 214503577-n-Pentyl-4-[1-(2-naphthylmethyl)-1,2,5,6-tetrahydropyrid-4-yl]-2,2-dimethylchroman-5-ol monohydrate

Product 1

HCID 214503634-Diethylaminobutyrate dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-n-pentyl-4-[1-(2-naphthylmethyl)-1,2,5,6-tetrahydropyrid-4-yl]-2,2-dimethylchroman-5-ol monohydrate (4.57g., prepared as described in Examples 2 and 3), 4-diethylaminobutyric acid hydrochloride (1.96g.) and dicyclohexylcarbodiimide (2.10g.) were dissolved together in dry dichloromethane (150 ml.) and the solution was stirred for 5 days at ambient temperature. The resulting precipitate of dicyclohexylurea was removed by filtration and the filtrate was evaporated to dryness in vacuo. The residual amorphous foam was dissolved in the minimum of ethanol and dry ether was added causing an off-white solid to be precipitated. This solid (2.90g.) was filtered off and the filtrate was treated with ethereal hydrogen chloride to give another off-white precipitate (2.86g.) which was collected by filtration. These two solids were combined and recrystallised from ethanol-ether to yield the desired 4-diethylaminobutyrate dihydrochloride as hygroscopic, off-white microcrystals (3.79g.), mp 96°C upwards (vague).

Workup

  1. customThe resulting precipitate of dicyclohexylurea was removed by filtration
  2. customthe filtrate was evaporated to dryness in vacuo
  3. dissolutionThe residual amorphous foam was dissolved in the minimum of ethanol and dry ether
  4. additionwas added
  5. customto be precipitated
  6. filtrationThis solid (2.90g.) was filtered off
  7. additionthe filtrate was treated with ethereal hydrogen chloride
  8. customto give another off-white precipitate (2.86g.) which
  9. filtrationwas collected by filtration
  10. customrecrystallised from ethanol-ether

Sources & evidence

ORD record
ord-854cfa3cef7b45daaaba872f0c55d6f2
Source dataset
uspto-grants-1976_06
Patent number
US03960880

Reaction notes

Loading…