Toluene → HCID 18186376, compound

HRID 1358048Notes

Reaction equation

HRID 1358048 reaction equation
Br[C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:14][CH:15]=3)[CH2:10][CH2:9][N:8]2[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)=[CH:4][CH:3]=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.C1(C)C=CC=CC=1.CC([O-])(C)C.[Na+]>[Cl-].[Na+].O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(OCC)C>[N:34]1([C:2]2[CH:33]=[CH:32][C:5]([CH2:6][CH:7]3[C:16]4[C:11](=[CH:12][C:13]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)=[CH:14][CH:15]=4)[CH2:10][CH2:9][N:8]3[C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:4][CH:3]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

9

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 18186409HCID 18186409, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 18186376HCID 18186376, compoundYield 49.3%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 3283Diethyl EtherSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

1-(4-Bromobenzyl)-6-phenylmethoxy-2-(4-fluorophenyl)-1,2,3,4-tetrahydroisoquinoline (0.82 g, 1.6 mmol) and piperidine (0.17 g, 1.96 mmol) are placed in a 100 ml round bottom flask containing anh. toluene (50 mL) under nitrogen. NaOtBu (0.22 g, 2.3 mmol), Pd(dba)2 (0.029 g, 2 mol %) and P(o-tolyl)3 (0.02 g, 6 mol %) are added, and the mixture heated to reflux overnight. The reaction is cooled to RT and treated with brine and ethyl ether. The organic layer is dried over MgSO4 and purified by column chromatography (SiO2, hexanes/ethyl acetate, 6:1) to yield the title compound (0.40 g, 49% yield): ES-MS (m/z) 507 [M+H]+.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux overnight
  3. dry with materialThe organic layer is dried over MgSO4
  4. custompurified by column chromatography (SiO2, hexanes/ethyl acetate, 6:1)

Sources & evidence

ORD record
ord-8ea45e42fd1245c1b3abb02b7b6bcd31
Source dataset
uspto-grants-2003_07
Patent number
US06593322B1

Reaction notes

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