Acetic Acid → (e)-3-(4-{[(1-Acetylpiperidin-4-yl)methylamino]methyl}phenyl)-n-(4'-chlorobiphenyl-4-yl)acrylamide

HRID 735179Notes

Reaction equation

HRID 735179 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:40])/[CH:23]=[CH:24]/[C:25]3[CH:30]=[CH:29][C:28]([CH2:31][N:32]([CH3:39])C4CCNCC4)=[CH:27][CH:26]=3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.[C:41](O)(=O)[CH3:42].F[C:46](F)(F)[C:47](O)=O.[NH3:52].[C:53](O)(=O)C>>[C:5]([N:52]1[CH2:42][CH2:41][CH:47]([CH2:39][NH:32][CH2:31][C:28]2[CH:27]=[CH:26][C:25](/[CH:24]=[CH:23]/[C:22]([NH:21][C:18]3[CH:19]=[CH:20][C:15]([C:12]4[CH:13]=[CH:14][C:9]([Cl:8])=[CH:10][CH:11]=4)=[CH:16][CH:17]=3)=[O:40])=[CH:30][CH:29]=2)[CH2:46][CH2:53]1)(=[O:7])[CH3:6]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 222AmmoniaHCID 7918Acetic AnhydrideHCID 23437676Trifluoroacetic acid acetateHCID 57845660(E)-N-(4'-chlorobiphenyl-4-yl)-3-{4[(methylpiperidin-4-ylamino)methyl]phenyl}acrylamide

Product 1

HCID 68817916(e)-3-(4-{[(1-Acetylpiperidin-4-yl)methylamino]methyl}phenyl)-n-(4'-chlorobiphenyl-4-yl)acrylamide

Procedure

0.017 mL (0.18 mmol) of acetic anhydride is added to a solution of 50 mg (0.087 mmol) of (E)—N-(4′-chlorobiphenyl-4-yl)-3-{4[(methylpiperidin-4-ylamino)methyl]phenyl}acrylamide×trifluoroacetic acid acetate in 4 mL of acetic acid and the mixture is stirred for 18 hours at ambient temperature. Then the reaction mixture is poured onto water and made basic with ammonia. The precipitate formed is suction filtered and washed with water. The product is dried at 60° C. in the circulating air dryer. Yield: 20 mg (46% of theory); C30H32ClN3O2 (M=502.05); melting point: 225° C.-226° C.; calc.: molecular ion peak (M+H)+: 502/504 (Cl); found: molecular ion peak (M+H)+: 502/504 (Cl).

Workup

  1. additionThen the reaction mixture is poured onto water
  2. customThe precipitate formed
  3. filtrationfiltered
  4. washwashed with water
  5. customThe product is dried at 60° C. in the circulating air dryer

Sources & evidence

ORD record
ord-694b3f36366040bdbd96936d47972cdd
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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