4-Nitrobenzoyl chloride → 4-Nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide

HRID 1659152Notes

Reaction equation

HRID 1659152 reaction equation
[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([NH:12][CH3:13])[CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](Cl)=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>>[N+:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([N:12]([CH:9]2[CH2:10][CH2:11][N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[CH2:8]2)[CH3:13])=[O:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

3

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 128957171-Cyclohexyl-N-methylpyrrolidin-3-amine

Product 1

HCID 128957184-Nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide

Procedure

4-Nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was prepared from 15 g. (0.085 mole) of 1-cyclohexyl-3-methylaminopyrrolidine and 15 g. (0.08 mole) p-nitrobenzoyl chloride. The 4-nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was converted to the fumarate salt (8.4 g., 24%) by precipitation with fumaric acid from isopropanol-isopropyl ether. The fumarate salt was dissolved in 95% ethanol and hydrogenated at three atmospheres of hydrogen over Raney Nickel for about two hours. The mixture was filtered, the filtrate concentrated and the residue partitioned between dilute sodium hydroxide and chloroform. The chloroform layer was dried and concentrated and the residue treated with hexamic acid in isopropanol-isopropyl ether. Recrystallization from the same solvent gave 5.2 g. (13.5% overall) of the salt melting 196°-199°C.

Workup

  1. customThe 4-nitro-N-(1-cyclohexyl-3-pyrrolidinyl)-N-methylbenzamide was converted to the fumarate salt (8.4 g., 24%) by precipitation with fumaric acid from isopropanol-isopropyl ether
  2. dissolutionThe fumarate salt was dissolved in 95% ethanol
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate concentrated
  5. customthe residue partitioned between dilute sodium hydroxide and chloroform
  6. dry with materialThe chloroform layer was dried
  7. concentrationconcentrated
  8. additionthe residue treated with hexamic acid in isopropanol-isopropyl ether
  9. customRecrystallization from the same solvent
  10. customgave 5.2 g
  11. custommelting 196°-199°C.

Sources & evidence

ORD record
ord-7d507217e7b74a5aace626f2e7c75a32
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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