Dimethylformamide → HCID 53668194, compound

HRID 2188219Notes

Reaction equation

HRID 2188219 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[C@@H:10]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:9]([CH2:20][NH:21][CH3:22])[CH2:8][CH2:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[CH3:34][O:35][C:36](=[O:40])[CH:37](Br)[CH3:38]>O>[CH3:34][O:35][C:36](=[O:40])[CH:37]([N:21]([CH3:22])[CH2:20][C@H:9]1[CH2:8][CH2:7][C:6]2[C:11](=[CH:12][CH:13]=[C:4]([O:3][CH3:2])[CH:5]=2)[C@H:10]1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[CH3:38]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 95576Methyl 2-bromopropionateHCID 70167236HCID 70167236, compound

Product 1

HCID 53668194HCID 53668194, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of cis-6-methoxy-2-methylaminomethyl-1-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride (1.00 g; prepared according to the procedures in Process 1), cesium carbonate (5.13 g) and N,N-dimethylformamide (20 cm3) was added methyl-2-bromopropionate (0.35 cm3) and the resultant mixture was stirred at 75° C. for 5 h. The reaction was then allowed to cool to room temperature and water (100 cm3) was added. The resulting mixture was extracted with diethyl ether (2×100 cm3) and the combined organic extracts were washed with water (100 cm3), dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product (1.11 g) was purified by column chromatography [basic alumina, eluting with toluene-hexane (1:1)] to afford the title compound as a gum (284 mg); positive ion ESI (M+H)+ 368.4.

Workup

  1. customprepared
  2. extractionThe resulting mixture was extracted with diethyl ether (2×100 cm3)
  3. washthe combined organic extracts were washed with water (100 cm3)
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product (1.11 g) was purified by column chromatography [basic alumina, eluting with toluene-hexane (1:1)]

Sources & evidence

ORD record
ord-c4b0d9dc660c41ffa5e0e0951a85a5ae
Source dataset
uspto-grants-2002_06
Patent number
US06410592B1

Reaction notes

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