Triethylamine → HCID 25174675, compound

HRID 2365939Notes

Reaction equation

HRID 2365939 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

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-5c659a4f74a44df19d7f10440690f8bc
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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