Tosylmethyl isocyanide → HCID 69280233, compound

HRID 968484Notes

Reaction equation

HRID 968484 reaction equation
[C:1]1([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([CH2:25][N+:26]#[C-])(=O)=O)=CC=1.CC(C)([O-])C.[K+]>CN(C=O)C.CC(O)(C)C.COCCOC.O>[C:1]1([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][CH:11]([C:25]#[N:26])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 3

HCID 161915Tosylmethyl isocyanideHCID 15143501-Benzyl-hexahydro-4H-azepin-4-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 69280233HCID 69280233, compoundYield 112%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of hexahydro-1-(phenylmethyl)-4H-azepin-4-one (0.2 mol) and 4-toluene-sulfonylmethyl isocyanide (0.25 mol) in DMF (200 ml) was stirred at 0° C. A solution of potassium tert-butoxide (0.4 mol) in a mixture of 2-methyl-2-propanol (200 ml) and 1,2-dimethoxyethane (200 ml) was added dropwise at 0° C. The mixture was allowed to reach room temperature and stirring was continued for 1 hour. The mixture was stirred in water and this mixture was extracted with DCM. The separated organic layer was dried, filtered and the solvent was evaporated, yielding 48 g of (±)-hexahydro-1-(phenylmethyl)-1H-azepine-4-carbonitrile (intermediate 1).

Workup

  1. additionwas added dropwise at 0° C
  2. customto reach room temperature
  3. stirringstirring
  4. extractionthis mixture was extracted with DCM
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-6da05282a77446aa948bc2b4fce5f471
Source dataset
uspto-grants-2007_12
Patent number
US07304052B2

Reaction notes

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