Sodium Hydroxide → HCID 20026482, compound

HRID 1723028Notes

Reaction equation

HRID 1723028 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[Br:21][CH2:22][C:23]1([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=2[Cl:41])[O:27][CH:26]([CH2:28]OS(C)(=O)=O)[CH2:25][O:24]1.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:21][CH2:22][C:23]1([C:34]2[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][C:35]=2[Cl:41])[O:27][CH:26]([CH2:28][O:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:13][CH2:12][N:11]([CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:10][CH2:9]3)=[CH:6][CH:7]=2)[CH2:25][O:24]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14074292HCID 14074292, compoundHCID 15576452HCID 15576452, compound

Product 1

HCID 20026482HCID 20026482, compoundYield 72.5%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3.77 g (14 mmol) of 4-(4-hydroxyphenyl)-1(pyrid-2-ylmethyl)piperazine, 200 ml of toluene, 5.88 g (14 mmol) of 2-bromomethyl-2-(2,4-dichlorophenyl)-4-methanesulfonyloxymethyl-1,3-dioxolane, 0.80 g of tetrabutylammonium bromide and 27 ml of 50% strength sodium hydroxide solution was stirred vigorously for 3 hours at 65° C. The phases were subsequently separated at room temperature. The toluene solution was shaken three times with water, dried, filtered and evaporated in vacuo. The residue remaining (8.8 g) was chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 28.0 cm) with elution using CH2Cl2 and CH2Cl2 /C2 5OH mixtures (to a maximum C2H5OH content of 4% by volume). After elution of a preliminary fraction (1.45 g), the fractions which were unary according to TLC were combined and evaporated in vacuo. 6.02 g (=72.4% yield) of 2-bromomethyl-2-(2,4-dichlorophenyl)-4-[4-(4-(pyrid-2-ylmethyl)piperazin-1-yl)phenoxymethyl]-1,3-dioxolane (cis/trans mixture) were obtained as a highly viscous oil, analysis: C27H28BrCl2N3O3 (MW 593.38) calc. C 54.65, H 4.76, Br 13.47, Cl 11.95, N 7.08; found C 53.5, H 4.9, Br 13.1, Cl 13.2, N 6.5%.

Workup

  1. customThe phases were subsequently separated at room temperature
  2. stirringThe toluene solution was shaken three times with water
  3. customdried
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customwas chromatographed on a silica gel S/CH2Cl2 column (diameter 2.6 cm, height 28.0 cm) with elution
  7. washAfter elution of a preliminary fraction (1.45 g)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-070d35859b0e4731a955920922627b45
Source dataset
uspto-grants-1989_08
Patent number
US04859670

Reaction notes

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