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Triethylamine → HCID 25174675, compound

HRID 453733
Notes
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Reaction equation

HRID 453733 reaction equation
Br[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][CH2:4]1.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]2)=[CH:16][CH:15]=1.C(N(CC)CC)C>C(#N)C>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[CH2:25][CH2:24][CH2:23][N:22]([CH2:2][CH:3]3[O:8][C:7]4[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=4[O:5][CH2:4]3)[CH2:21]2)=[CH:18][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 983332-Bromomethyl-1,4-benzodioxaneHCID 203645753-(4-Chlorophenyl)Piperidine

Product 1

HCID 25174675HCID 25174675, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2-bromomethyl-2,3-dihydrobenzo[1,4]dioxine (34 mg, 0.15 mmol), 3-(4-chloro-phenyl)piperidine (38 mg, 0.165 mmol) and triethylamine (38 mg, 0.38 mmol) in acetonitrile (2 ml) was heated in a microwave reactor at 110-150° C. for 290 min. After evaporation to dryness, the crude product was purified by flash chromatography using a gradient of heptane and EtOAc as eluent to give 36 mg of the title compound.

Workup

  1. customAfter evaporation to dryness
  2. customthe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-5c8765487eec4b709e3716c6b58db049
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492549B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes