Sodium Hydroxide → HCID 19012192, compound

HRID 1974947Notes

Reaction equation

HRID 1974947 reaction equation
[C:1]([CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][S:7](Cl)(=[O:9])=[O:8])([O:3][CH3:4])=[O:2].[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Na+]>ClCCl>[CH2:11]([CH:5]([CH2:6][S:7]([N:28]1[CH2:29][CH2:30][N:25]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:26][CH2:27]1)(=[O:9])=[O:8])[C:1]([O:3][CH3:4])=[O:2])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 759941-BenzylpiperazineHCID 22403010HCID 22403010, compound

Product 1

HCID 19012192HCID 19012192, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 3 L round bottom flask was added the resultant compound from Example 1E (370.5 g, 1.34 mol) and dichloromethane (2 L). The mixture was cooled to 0° C. in an ice water bath and a solution of N-benzyl piperazine (295.8 g, 1.68 mol) was added dropwise with vigorous stirring over 2 h. After the addition was completed, the mixture was stirred an additional 4 h while at 0° C. The solution was then poured into a separatory funnel containing 2 L of a 5% aqueous NaOH solution. The layers were partitioned and the organic layer was dried over potassium carbonate. Concentration in vacuo yielded an oil, which was filtered through 1 kg of silica gel using 3:2 hexane/ethyl acetate as an eluant. Concentration gave 467 g (84%) of the desired product: 1H NMR (CDCl3) δ 7.37-7.12 (m, 10H), 3.66 (s, 3H), 3.51 (s, 2H), 3.42 (dd, 1H), 3.29-3.13 (m, 5H), 3.06 (dd, 1H), 2.96-2.84 (m, 2H), 2.50-2.42 (m, 4H).

Workup

  1. additionAfter the addition
  2. stirringthe mixture was stirred an additional 4 h while at 0° C
  3. additionThe solution was then poured into a separatory funnel
  4. customThe layers were partitioned
  5. dry with materialthe organic layer was dried over potassium carbonate
  6. concentrationConcentration in vacuo
  7. customyielded an oil, which
  8. filtrationwas filtered through 1 kg of silica gel using 3:2 hexane/ethyl acetate as an eluant
  9. concentrationConcentration

Sources & evidence

ORD record
ord-f688a982712543c2b415f7dd2144645f
Source dataset
uspto-grants-1994_02
Patent number
US05284849

Reaction notes

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