Hydrochloric Acid → 6-(Cyanomethyl)-2,3-dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine]

HRID 1741033Notes

Reaction equation

HRID 1741033 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]2([C:11]3[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:10]=3[O:9][CH2:8]2)[CH2:4][CH2:3]1.ClC1C=CC(O[CH2:25][C:26]#[N:27])=CC=1.CC(C)([O-])C.[K+].Cl>CN(C=O)C.O>[C:26]([CH2:25][C:14]1[C:13]([N+:16]([O-:18])=[O:17])=[CH:12][C:11]2[C:5]3([CH2:8][O:9][C:10]=2[CH:15]=1)[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)#[N:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 105385022,3-Dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine]HCID 23665647Potassium tert-butoxide

Product 1

HCID 186900676-(Cyanomethyl)-2,3-dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine]Yield 43.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-1'-methyl-5-nitrospiro[benzofuran-3,4'-piperidine] (D4, 0.70 g, 2.8 mmol) and 4-chlorophenoxyacetonitrile (0.90 g, 5.4 mmol) were dissolved in dry DMF (15 ml) and added to potassium t-butoxide (1.60 g, 14.3 mmol). The mixture was stirred under Ar for 6 h, diluted with water (150 ml), acidified (5M HCl) and washed with ethyl acetate. It was then basified (saturated K2CO3 solution) and extracted with ethyl acetate. This extract was dried (Na2SO4) and evaporated to give the title compound (0.35 g, 43%) still containing some spirocyclic starting material (ca 30%, NMR).

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. dry with materialThis extract was dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-faf7daee96834e59bec7dd25cdbefa36
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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