Ethanol → 4-(Benzyloxy)-3-{2-[1-(ethoxymethyl)piperidin-4-yl]ethoxy}-1,2-benzisoxazole

HRID 2410328Notes

Reaction equation

HRID 2410328 reaction equation
[CH2:1]([O:8][C:9]1[C:14]2[C:15]([O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)=[N:16][O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27](=O)([O-])[O-].[K+].[K+].C=O.[CH2:35]([OH:37])[CH3:36]>>[CH2:1]([O:8][C:9]1[C:14]2[C:15]([O:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][N:24]([CH2:27][O:37][CH2:35][CH3:36])[CH2:23][CH2:22]3)=[N:16][O:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 693162454-(Benzyloxy)-3-(2-piperidin-4-ylethoxy)-1,2-benzisoxazole

Product 1

HCID 693157784-(Benzyloxy)-3-{2-[1-(ethoxymethyl)piperidin-4-yl]ethoxy}-1,2-benzisoxazole

Procedure

To a stirred mixture of 4-(benzyloxy)-3-(2-piperidin-4-ylethoxy)-1,2-benzisoxazole (3.1 g, 8.4 mmol, EXAMPLE 7, Step 3) and potassium carbonate (1.2 g, 8.4 mmol) in ethanol (16.0 mL) was added paraformaldehyde (0.28 g, 9.2 mmol) at ambient temperature. After being stirred at room temperature for 14 h, the mixture was filtered. The filtrate was concentrated in vacuo to give 3.4 g (quant.) of the title compound as a colorless oil.

Workup

  1. filtrationthe mixture was filtered
  2. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-400f995b9c56452e96c696b1786f6c09
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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