Water → HCID 53713365, compound

HRID 1651619Notes

Reaction equation

HRID 1651619 reaction equation
[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[NH:16][C:12]4=[C:13]([CH2:14]3)[C:8](=[C:9]1[CH2:10][CH2:11]4)[CH:7]=[CH:6][CH2:5][N:4]=[CH:3]2.[CH:19](N(C(C)C)CC)([CH3:21])[CH3:20].C(Br)C=C.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]12[CH:17]([CH3:18])[CH:15]3[N:16]([CH2:21][CH:19]=[CH2:20])[C:12]4=[C:13]([CH2:14]3)[C:8](=[C:9]1[CH2:10][CH2:11]4)[CH:7]=[CH:6][CH2:5][N:4]=[CH:3]2

Participants

7

Reactant 4

HCID 962WaterHCID 7841Allyl bromideHCID 81531DiisopropylethylamineHCID 73656243HCID 73656243, compound

Product 1

HCID 53713365HCID 53713365, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 1.86 g of 6,12-dimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-9H-pyrrolo[3,2-h][3]benzazocine and 40 ml of dimethylformamide was added 2.85 ml of diisopropylethyl amine. The mixture was cooled to 0° C. and 0.78 ml of allyl bromide in 5.0 ml of dimethylformamide was added, with stirring under nitrogen. The mixture was stirred at 0° for 4.5 hr and then poured into water and ethyl acetate. The layers were separated and the aqueous layer extracted with ethyl acetate and ether. The combined organic layers were washed with brine, dried over anhydrous potassium carbonate, filtered and, the filtrate was concentrated. The residue was purified by flash column chromatography on silica gel (2% triethylamine/0-10% methanol/ether) and on alumina (ether) to afford 1.02 g (47%) of product. Recrystallization from ether-pentane gave the analytical sample, mp 165°-168° C.

Workup

  1. stirringThe mixture was stirred at 0° for 4.5 hr
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with ethyl acetate and ether
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by flash column chromatography on silica gel (2% triethylamine/0-10% methanol/ether) and on alumina (ether)

Sources & evidence

ORD record
ord-f68a86bd78824665a40ce751cfb87f4b
Source dataset
uspto-grants-1990_05
Patent number
US04929622

Reaction notes

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