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Methanol → 4-(5-Bromo-2,3-dihydrobenzofuran-2-yl)piperidine

HRID 1622247
Notes
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Reaction equation

HRID 1622247 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH:14]([CH:16]3[CH2:21][CH2:20][N:19](C(=O)C(F)(F)F)[CH2:18][CH2:17]3)[CH2:13][C:12]=2[CH:28]=1.CO.O>[Cl-].[Na+].O>[Br:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][CH:14]([CH:16]3[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[CH2:13][C:12]=2[CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 866748871-[4-(5-Bromo-2,3-dihydro-benzofuran-2-yl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 674691344-(5-Bromo-2,3-dihydrobenzofuran-2-yl)piperidine

Reagents, catalysts & solvents 1

HCID 57417360
Sodium chloride; water
Solvent

Procedure

Potassium carbonate (10.17 g) is added to an ice-cooled mixture of 1-[4-(5-bromo-2,3-dihydro-benzofuran-2-yl)-piperidin-1-yl]-2,2,2-trifluoro-ethanone (4.64 g), methanol (120 mL), and water (30 mL). The reaction mixture is stirred over night at room temperature. Brine (150 mL) is added and the mixture is extracted with dichloromethane. The combined organic phases are dried over MgSO4 and concentrated in vacuo. The crude product is used for the next step without further purification. LC (method 2): tR=1.05 min; Mass spectrum (ESI+): m/z=282, 284 [M+H]+.

Workup

  1. temperaturecooled
  2. extractionthe mixture is extracted with dichloromethane
  3. dry with materialThe combined organic phases are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product is used for the next step without further purification

Sources & evidence

ORD record
ord-ff506c79a105489fb15868d182e049bc
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08778926B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes