Toluene → HCID 69515628, compound

HRID 1180202Notes

Reaction equation

HRID 1180202 reaction equation
BrC1C=C[C:5]([CH2:6][CH:7]2[C:16]3[C:11](=[CH:12][C:13](OCC4C=CC=CC=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)=CC=1.[NH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.[CH3:47][C:48]([O-])(C)C.[Na+].[CH2:53]([O:55][CH2:56][CH3:57])C>[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>[N:34]1([C:43]2[CH:44]=[CH:45][C:40]([CH2:46][CH2:53][O:55][CH:56]3[C:57]4[C:11](=[CH:12][C:13]([C:14]5[CH:5]=[CH:6][CH:7]=[CH:16][CH:15]=5)=[CH:47][CH:48]=4)[CH2:10][CH2:9][N:8]3[C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)=[CH:41][CH:42]=2)[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

9

Reactant 5

HCID 1140TolueneHCID 3283Diethyl EtherHCID 8082PiperidineHCID 18186409HCID 18186409, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 69515628HCID 69515628, compoundYield 49%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 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-6c3bbf8624ad457aa279e6ac7476f678
Source dataset
uspto-grants-2007_10
Patent number
US07279489B2

Reaction notes

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