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

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

Reactant 4

HCID 702Ethanol

HCID 712Formaldehyde

HCID 11430Potassium Carbonate

HCID 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.