Ammonia → HCID 178513942, compound

HRID 1463743Notes

Reaction equation

HRID 1463743 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([OH:22])=O)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1.ClC(OCC)=O.[NH3:29]>C(Cl)(Cl)Cl>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([C:20]([NH2:29])=[O:22])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10928Ethyl chloroformateHCID 178525711HCID 178525711, compound

Product 1

HCID 178513942HCID 178513942, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

18 g of trans-4-[trans-4-(2-(1,3-dioxolan-2-yl)ethyl]-cyclohexyl)cyclohexanecarboxylic acid were dissolved in 600 ml of chloroform while gassing with argon and the solution was treated dropwise at 0° C. while stirring within 3 minutes with a solution of 7.2 ml of ethyl chloroformate in 40 ml of chloroform. The reaction solution was stirred for a further 30 minutes. Ammonia gas was then conducted into the solution during 10 minutes. The mixture was stirred at 0° C. for a further 30 minutes and then extracted twice with 300 ml of water each time. The aqueous phases were back-extracted with 100 ml of chloroform each time. The combined organic phases were dried over magnesium sulfate, filtered and evaporated. Recrystallization of the brown crystalline crude product obtained (19 g) from 800 ml of methylene chloride gave 13 g of trans-4-[trans-4-[2-(1,3-dioxolan-2-yl)ethyl]-cyclohexyl]cyclohexanecarboxamide as pale brown crystals.

Workup

  1. additionthe solution was treated dropwise at 0° C.
  2. stirringThe mixture was stirred at 0° C. for a further 30 minutes
  3. extractionextracted twice with 300 ml of water each time
  4. extractionThe aqueous phases were back-extracted with 100 ml of chloroform each time
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customRecrystallization of the brown crystalline crude product
  9. customobtained (19 g) from 800 ml of methylene chloride

Sources & evidence

ORD record
ord-1ab72fc4a37f4859ac7da58ee1c84fe7
Source dataset
uspto-grants-1994_04
Patent number
US05302317

Reaction notes

Loading…