3-(4-Piperidyl)-6-fluoro-1,2-benzisoxazole → 3-{2-[4-(6-Fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one

HRID 1271536Notes

Reaction equation

HRID 1271536 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][N:5]2[C:6](=[O:11])[C:7]=1[CH2:8][CH:9]=O.[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[N:22][O:23][C:19]=2[CH:18]=1>C1(C)C=CC=CC=1>[F:16][C:17]1[CH:31]=[CH:30][C:20]2[C:21]([CH:24]3[CH2:25][CH2:26][N:27]([CH:9]=[CH:8][C:7]4[C:6](=[O:11])[N:5]5[CH2:12][CH2:13][CH2:14][CH2:15][C:4]5=[N:3][C:2]=4[CH3:1])[CH2:28][CH2:29]3)=[N:22][O:23][C:19]=2[CH:18]=1

Participants

4

Reactant 2

HCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 102144672-(2-Methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)acetaldehyde

Product 1

HCID 865989853-{2-[4-(6-Fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-oneYield 97.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.96 g (14.33 mmoles) of (2-methyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-3-yl)-acetaldehyde (II), 3.16 g (14.33 mmoles) of 6-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (IV) and 50 mL of toluene was transferred to a Dean Stark apparatus. The mixture was brought to boiling point, refluxed for 3 hours, and the solvent was evaporated under reduced pressure to give 5.70 g (97.3%) of 3-{2-[4-(6-fluorobenzo[d]isoxazol-3-yl)-piperidin-1-yl]-vinyl}-2-methyl-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one (III) as a deep orange solid. The compound thus obtained was pure enough as to be used in the subsequent reaction step with no prior purification or optionally crystallized from an organic solvent, preferably ethanol.

Workup

  1. temperaturerefluxed for 3 hours
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-74beb3eedc224da1a6161a1fe29467c7
Source dataset
uspto-grants-2007_04
Patent number
US07205405B2

Reaction notes

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