Acetic Acid → 4-(6-Chloronaphthalene-2-sulfonyl)-1-{ethyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

HRID 2086285Notes

Reaction equation

HRID 2086285 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.[BH4-].[Na+].[C:37](O)(=O)[CH3:38]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([N:21]([CH2:37][CH3:38])[CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[O:34])[CH2:16]1)(=[O:13])=[O:14])[CH:6]=[CH:5]2

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 178254104-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone

Product 1

HCID 227271194-(6-Chloronaphthalene-2-sulfonyl)-1-{ethyl[1-(4-pyridyl)-4-piperidinyl]amino}-2-piperazinone

Procedure

(Method B) 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino]-2-piperazinone (14 g) was dissolved in acetic acid (160 ml) and the reaction mixture was treated portionwise with sodium borohydride (11.36 g) while keeping the temperature at 20° C., and then stirred at room temperature for 15 hours. The reaction mixture was concentrated and the residue was made alkaline by adding an aqueous solution of sodium hydroxide, extracted with dichloromethane, dried and concentrated. The residue obtained was crystallized from ethanol to obtain the title compound (12.96 g) as colorless crystals.

Workup

  1. customat 20° C.
  2. concentrationThe reaction mixture was concentrated
  3. additionby adding an aqueous solution of sodium hydroxide
  4. extractionextracted with dichloromethane
  5. customdried
  6. concentrationconcentrated
  7. customThe residue obtained
  8. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-1c87c4d01b5a426abb3273c9e1d2896a
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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