Chloroacetonitrile → HCID 86740000, compound

HRID 1381158Notes

Reaction equation

HRID 1381158 reaction equation
[C:1]1([C@@:7]23[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C@@H:8]2[CH2:9][NH:10][CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:27][C:28]#[N:29]>CN(C)C=O.CCOCC>[C:28]([CH2:27][N:10]1[CH2:11][CH2:12][C@:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[C@@H:8]2[CH2:9]1)#[N:29]

Participants

6

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 86739997HCID 86739997, compound

Product 1

HCID 86740000HCID 86740000, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.02 g of cis-1,2,3,4,4a,9b-hexahydro-4a-phenyl-benzofuro[3,2-c]pyridine in 48 ml of dry dimethylformamide was added 3.6 g of anhydrous potassium carbonate and 0.982 g of chloroacetonitrile. The resulting suspension was heated at 80° under nitrogen for 19 hours. The cooled reaction mixture was diluted with 500 ml of ether and washed with water (4×250 ml). The organic layer was dried over anhydrous Na2SO4 and evaporated in vacuo to give 3.48 g (99.9%) of a gum, which crystallized on standing. A 0.35 g portion of this material was recrystallized from ethanol to afford 0.22 g of crystals, m.p. s 93, 94°-96°.

Workup

  1. temperatureThe resulting suspension was heated at 80° under nitrogen for 19 hours
  2. customThe cooled reaction mixture
  3. washwashed with water (4×250 ml)
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-283541693d3348fd84cae8b024f404c3
Source dataset
uspto-grants-1986_04
Patent number
US04585779

Reaction notes

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