Dimethylformamide → HCID 70168185, compound

HRID 2188215Notes

Reaction equation

HRID 2188215 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7]([CH2:14][NH:15][CH2:16][C@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:27])[CH:23]=2)[C@H:18]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)C=O.[CH2:39](Br)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O>[CH2:7]([CH2:14][NH:15][CH2:16][C@H:17]1[CH2:26][CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:27][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH:23]=2)[C@H:18]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 70168151HCID 70168151, compound

Product 1

HCID 70168185HCID 70168185, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of cesium carbonate (1.09 g), cis-2-(N-benzylmethylamino)methyl-6-hydroxy-1-phenyl-1,2,3,4-tetrahydronaphthalene (600 mg) and N,N-dimethylformamide (10 cm3) was added benzyl bromide (0.236 cm3). The resulting mixture was warmed to 80° C. and stirred for 2 h. Upon cooling, water (50 cm3) was added and the aqueous mass was extracted with ether (2×50 cm3). The combined ether extracts were washed with water (30 cm3), dried (Na2SO4), filtered and the solvent was evaporated under reduced pressure to afford a yellow oil. This was purified by column chromatography [silica, eluting with petroleum ether (b.p. 40-60° C.)-ethyl acetate (15:1)] to afford the title compound (538 mg; 72%) as a light yellow oil.

Workup

  1. temperatureUpon cooling
  2. extractionthe aqueous mass was extracted with ether (2×50 cm3)
  3. washThe combined ether extracts were washed with water (30 cm3)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure
  7. customto afford a yellow oil
  8. customThis was purified by column chromatography [silica, eluting with petroleum ether (b.p. 40-60° C.)-ethyl acetate (15:1)]

Sources & evidence

ORD record
ord-ef982b45098d4cbd89db2e4c8df21237
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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