Hydrochloric Acid → 2-(1-Piperazinyl)-4-(1-pyrrolidinyl)benzenamine

HRID 2372614Notes

Reaction equation

HRID 2372614 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([O-])=O.Cl.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[N:15]1[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3119336HCID 3119336, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 224188132-(1-Piperazinyl)-4-(1-pyrrolidinyl)benzenamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-nitro-2-piperazinyl-4-pyrrolidinylbenzene (4.57 g), ethanol (110 ml), hydrochloric acid (1.2N, 6 ml) and palladium on carbon (10%, 1 g) is exposed to hydrogen 51 psi at 20°-25° in a Parr flask. After 16 h (49 psi total uptake) the mixture is filtered. Basic workup (chloroform, potassium carbonate) and column chromatography silica gel (50 g) eluting with chloroform/methanol (4/1) gives the title compound as an oil. IR (nujol) 3315, 2947, 2816, 1512, 1258, 1001 and 753 cm-1 ; NMR (CDCl3) 1.8-2.0, 2.9-3.2, 6.52 and 6.6-6.8 δ; MS (electron impact) 246, 204 and 189.

Workup

  1. filtrationAfter 16 h (49 psi total uptake) the mixture is filtered
  2. washBasic workup (chloroform, potassium carbonate) and column chromatography silica gel (50 g) eluting with chloroform/methanol (4/1)

Sources & evidence

ORD record
ord-7c3371067f4942ad831a6803b3f470ac
Source dataset
uspto-grants-1992_03
Patent number
US05099019

Reaction notes

Loading…