Acetic Anhydride → HCID 178484975, compound

HRID 1722694Notes

Reaction equation

HRID 1722694 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[N:25]2[CH2:30][CH2:29][CH:28]([N:31]([CH3:36])[C:32]([NH:34][CH3:35])=[NH:33])[CH2:27][CH2:26]2)=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)Cl>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[N:18]=[C:17]2[N:25]2[CH2:26][CH2:27][CH:28]([N:31]([CH3:36])[C:32]([NH:34][CH3:35])=[N:33][C:5](=[O:7])[CH3:6])[CH2:29][CH2:30]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 178485111HCID 178485111, compound

Product 1

HCID 178484975HCID 178484975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

0.48 ml of acetic anhydride dissolved in 5 ml of methylene chloride is added to a solution of 2 g (0.005 mole) of N-[1-[1-[(4-fluorophenyl)methyl]-2-(1H)-benzimidazolyl]-4-piperidinyl]-N,N'-dimethylguanidine in 20 ml of methylene chloride, cooled to 5° C. Stirring is continued for 2 h and the mixture is then poured into concentrated sodium hydroxide. The phases are separated, the organic phase is dried with MgSO4, is filtered and is evaporated down. On addition of acetone, the product crystallizes. It is purified by chromatography on a silica column (eluent 9/1 methylene chloride/methanol) N-[1-[1-[(4-fluorophenyl)methyl]-2(1H)-benzimidazolyl]-4-piperidinyl]-N,N'-dimethyl-N"-acetylguanidine is obtained.

Workup

  1. customThe phases are separated
  2. dry with materialthe organic phase is dried with MgSO4
  3. filtrationis filtered
  4. customis evaporated down
  5. additionOn addition of acetone
  6. customthe product crystallizes
  7. customIt is purified by chromatography on a silica column (eluent 9/1 methylene chloride/methanol) N-[1-[1-[(4-fluorophenyl)methyl]-2(1H)-benzimidazolyl]-4-piperidinyl]-N,N'-dimethyl-N"-acetylguanidine
  8. customis obtained

Sources & evidence

ORD record
ord-93c15a8c776341abb96161de54886cbe
Source dataset
uspto-grants-1989_08
Patent number
US04857536

Reaction notes

Loading…