Ammonia → HCID 67821517, compound

HRID 1198638Notes

Reaction equation

HRID 1198638 reaction equation
[C:1]1(=[C:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.N.[CH3:13][N:14]([CH3:18])CC[Cl:17].Cl.[C:20]1(C)C=CC=C[CH:21]=1>>[ClH:17].[C:4]1([CH:5]([N:14]([CH3:18])[CH3:13])[CH2:1][CH:6]2[CH2:10][CH2:9][CH2:8][C:7]2=[O:11])[CH2:3][CH2:2][CH2:21][CH:20]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 1140TolueneHCID 79012-Chloro-N,N-dimethylethylamineHCID 69995Cyclopentylidenecyclopentan-2-one

Product 1

HCID 67821517HCID 67821517, compound

Conditions

Temperature
100 °C

Procedure

To a suspension of 1.90 g (41 mmole) of NaNH2 in 60 ml of dry toluene, 5.50 g (35 mmole) of 2-cyclopentylidene cyclopentanone was added dropwise below about 30° C. under stirring. The resulting mixture was stirred at about room temperature until no NH3 was evolved and then 3.8 g (32 mmole) of 2-dimethylaminoethyl chloride was added dropwise. The mixture was heated for about 2 hours at about 100° C. under stirring. On cooling, the mixture was acidified with 2N HCl. The aqueous layer was separated and the organic layer was extracted with 2N HCl. The combined aqueous layer was basified with 10% NaOH and extracted with ether. The ether extracts were dried over anhydrous MgSO4. The ether solution was treated with ethanolic hydrogen chloride to give 2-(1-cyclopenten-1-yl)-2-dimethylamino-ethyl cyclopentanone hydrochloride.

Workup

  1. additionwas added dropwise below about 30° C.
  2. stirringunder stirring
  3. temperatureOn cooling
  4. customThe aqueous layer was separated
  5. extractionthe organic layer was extracted with 2N HCl
  6. extractionextracted with ether
  7. dry with materialThe ether extracts were dried over anhydrous MgSO4
  8. additionThe ether solution was treated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-ab9bb9b263a74ed48ba6de41fea2b985
Source dataset
uspto-grants-1994_01
Patent number
US05281622

Reaction notes

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