Hydrochloric Acid → HCID 20385596, compound

HRID 46896Notes

Reaction equation

HRID 46896 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[N:20](C(C)=C)[C:19]3=[O:30])[CH2:11][CH2:10]2)=[C:4]([N+:31]([O-:33])=[O:32])[CH:3]=1.CC1C=CC=CC=1.Cl>CC(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][N:18]3[C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=4[NH:20][C:19]3=[O:30])[CH2:13][CH2:14]2)=[C:4]([N+:31]([O-:33])=[O:32])[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 203856271-[3-{4-[(4-chloro-2-nitrophenyl)amino]-1-piperidinyl}propyl]-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one

Product 1

HCID 20385596HCID 20385596, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 98.5 parts of 1-[3-{4-[(4-chloro-2-nitrophenyl)amino]-1-piperidinyl}propyl]-1,3-dihydro-3-(1-methylethenyl)-2H-benzimidazol-2-one in 360 parts of methylbenzene is acidified with 2-propanol, previously saturated with gaseous hydrogen chloride. After boiling for a while, an oil precipitates. The supernatant phase is decanted and the residual oil is suspended in water. The suspension is alkalized with a concentrated ammonium hydroxide solution. The product is extracted with methylbenzene. The extract is dried, filtered and evaporated. The residue is crystallized from 4-methyl-2-pentanone. The product is filtered off and dried, yielding 68 parts (75.5%) of 1-[3-{4-[(4-chloro-2-nitrophenyl)amino]-1-piperidinyl}-propyl]-1,3-dihydro-2H-benzimidazol-2-one.

Workup

  1. customan oil precipitates
  2. customThe supernatant phase is decanted
  3. extractionThe product is extracted with methylbenzene
  4. customThe extract is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is crystallized from 4-methyl-2-pentanone
  8. filtrationThe product is filtered off
  9. customdried

Sources & evidence

ORD record
ord-90d5bdd3e7b34493993bf9744ef4a32b
Source dataset
uspto-grants-1979_11
Patent number
US04175129

Reaction notes

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