Lithium borohydride → 4-[(6-Chloro-2-naphthyl)sulfonyl]-6-(hydoxymethyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone hydrochloride

HRID 2086304Notes

Reaction equation

HRID 2086304 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:21][C:20](=[O:22])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:29][CH2:28][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:26][CH2:25]3)[CH:18]([C:37](OC)=[O:38])[CH2:17]1)(=[O:15])=[O:14])[CH:7]=[CH:6]2.[BH4-].[Li+].Cl.CO>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([S:13]([N:16]1[CH2:17][CH:18]([CH2:37][OH:38])[N:19]([N:23]([CH3:36])[CH:24]3[CH2:25][CH2:26][N:27]([C:30]4[CH:35]=[CH:34][N:33]=[CH:32][CH:31]=4)[CH2:28][CH2:29]3)[C:20](=[O:22])[CH2:21]1)(=[O:14])=[O:15])[CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 4148881Lithium borohydrideHCID 21893726Hydrochloride methanolHCID 22727077Methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride

Product 1

HCID 227272524-[(6-Chloro-2-naphthyl)sulfonyl]-6-(hydoxymethyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-2-piperazinone hydrochlorideYield 83.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 4-[(6-chloro-2-naphthyl)sulfonyl)-1-[methyl[1-(4-pyridinyl)-4-piperidinyl]amino]-6-oxo-2-piperazinecarboxylate hydrochloride (0.3 g) in methanol (20 ml) was treated with 3 portions of lithium borohydride (1.14 g) with stirring at 0° C. After completion of the reaction, the reaction system was adjusted at pH 4 with a 10% hydrochloric acid/methanol solution, and then concentrated under reduced pressure. The residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate, and the organic phase was dried over magnesium sulfate, and then concentrated under reduced pressure. The residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile) to obtain the title compound (0.12 g) as a colorless powder.

Workup

  1. customAfter completion of the reaction
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between methylene chloride and saturated aqueous sodium bicarbonate
  4. dry with materialthe organic phase was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified on a CHP-20 column (water→1% 1N hydrochloric acid-containing 30% aqueous solution of acetonitrile)

Sources & evidence

ORD record
ord-988f8499adfc4b728093ef425ac0f44e
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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