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Water → 1-{1-[3-(4-Methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-4-methyl-piperazine

HRID 2378051
Notes
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Reaction equation

HRID 2378051 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:14]([C:22]3(C=O)[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:7][CH:6]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[C:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:14]([C:22]3([CH2:27][N:28]4[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]4)[CH2:24][CH2:23]3)[O:13][N:12]=2)=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 531671-Methylpiperazine2×HCID 5049666Sodium triacetoxyborohydride2×HCID 86613309HCID 86613309, compound

Product 1

HCID 689564541-{1-[3-(4-Methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-4-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture consisting of 1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]cyclopropanecarbaldehyde (this example, Step A, 0.490 g) in dichloromethane (15 mL) is added 1-methyl-piperazine (0.173 mL) and sodium triacetoxyborohydride (0.420 g.) The mixture is stirred for two hours. Another portion of 1-methyl-piperazine (0.08 mL) and sodium triacetoxyborohydride (0.18 g) are added to the mixture and the mixture is stirred overnight. The mixture is treated with water and is extracted with dichloromethane. The organic layer is separated and is dried over anhydrous sodium sulfate. The mixture is filtered and the filtrate is concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography to afford 1-{1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-4-methyl-piperazine (0.500 g.)

Workup

  1. stirringthe mixture is stirred overnight
  2. extractionis extracted with dichloromethane
  3. customThe organic layer is separated
  4. dry with materialis dried over anhydrous sodium sulfate
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customThe concentrate is purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-74fcb21d714a430c9dd748c7ff8e4ad9
Source dataset
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07470715B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes