Isatoic Anhydride → HCID 14013288, compound

HRID 2309650Notes

Reaction equation

HRID 2309650 reaction equation
[NH:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[C:4](=[O:11])OC1=O.[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[CH2:18][N:19]1[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[N:21]=[C:20]1[CH2:28][CH:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][NH2:37])[CH2:31][CH2:30]1>CN(C)C=O>[NH2:1][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[C:4]([NH:37][CH2:36][CH2:35][N:32]1[CH2:33][CH2:34][CH:29]([CH2:28][C:20]2[N:19]([CH2:18][C:14]3[O:13][CH:17]=[CH:16][CH:15]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:21]=2)[CH2:30][CH2:31]1)=[O:11]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 14012960HCID 14012960, compound

Product 1

HCID 14013288HCID 14013288, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of 4.9 parts of 2H-3,1-benzoxazine-2,4(1H)-dione and 45 parts of N,N-dimethylformamide were added dropwise 10.15 parts of 4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidineethanamine and 45 parts of C at 50° C. Upon completion, stirring was continued for 4 hours at 70° C. After cooling, the reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 1,1'-oxybisethane. The product was filtered off and dried, yielding 10 parts (73%) of 2-amino-N-[2-[4-[[1-(2-furanylmethyl)-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]benzamide; mp. 125.7° C. (466).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was evaporated
  3. customThe residue was purified by column chromatography over silica gel using
  4. additiona mixture of trichloromethane and methanol
  5. customThe pure fractions were collected
  6. customthe eluent was evaporated
  7. customThe residue was crystallized from 1,1'-oxybisethane
  8. filtrationThe product was filtered off
  9. customdried

Sources & evidence

ORD record
ord-f595c9e0d003469eb03ba50dacdb8b47
Source dataset
uspto-grants-1987_09
Patent number
US04695575

Reaction notes

Loading…