Sodium Hydroxide → HCID 19887612, compound

HRID 1073840Notes

Reaction equation

HRID 1073840 reaction equation
[C:1]([NH:4][CH2:5][C:6]([C:8]12[CH2:15][N:12]([CH2:13][CH2:14]1)[CH2:11][CH2:10][CH2:9]2)=[O:7])(=O)[CH3:2].[OH-].[Na+]>>[CH3:2][C:1]1[O:7][C:6]([C:8]23[CH2:15][N:12]([CH2:13][CH2:14]2)[CH2:11][CH2:10][CH2:9]3)=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 22156782HCID 22156782, compound

Product 1

HCID 19887612HCID 19887612, compound

Conditions

Temperature
160 °C

Procedure

A mixture of 5-[α-(acetylamino)acetyl]-1-azabicyclo[3.2.1]octane (D29) (0.12 g, 0.57 mmole) and polyphosphoric acid (6.0 g) under nitrogen was placed in an oil bath at 110° C. and heated to 160° C. over a period of 15 min. The temperature was maintained at this level for a further 15 min and the reaction was then poured onto ice. After basifying with 40% sodium hydroxide the solution was saturated with potassium 5 carbonate and extracted into chloroform (4×20 ml). Concentration of the dried (sodium sulphate) organic layers followed by purification on neutral alumina using a graded eluant of 5-10% methanol in ethyl acetate afforded the title compound (E26) as a colourless oil (40mg; 36%).

Workup

  1. customwas placed in an oil bath at 110° C.
  2. temperatureThe temperature was maintained at this level for a further 15 min
  3. additionthe reaction was then poured onto ice
  4. extractionextracted into chloroform (4×20 ml)
  5. dry with materialConcentration of the dried (sodium sulphate) organic layers
  6. customfollowed by purification on neutral alumina using a graded eluant of 5-10% methanol in ethyl acetate

Sources & evidence

ORD record
ord-f3c6244cf8724d51bd51bba2b474ad97
Source dataset
uspto-grants-1990_11
Patent number
US04971975

Reaction notes

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