Dimethylformamide → HCID 20143719, compound

HRID 280986Notes

Reaction equation

HRID 280986 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=[O:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[CH2:31](I)[CH3:32].CN(C)C=O>O>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH2:31][CH3:32])=[O:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340Iodoethane2×HCID 516892Sodium Bicarbonate2×HCID 20143674HCID 20143674, compound

Product 1

HCID 20143719HCID 20143719, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(1-benzyloxycarbonyl-4-piperidyl)heptanoic acid (6.4 g), sodium bicarbonate (3.1 g) and ethyl iodide (8.6 g) and N,N-dimethylformamide (20 ml) is stirred for 3 hours at 100° C. After further addition of ethyl iodide (2.9 g) and sodium bicarbonate (1 g), the stirring is continued for further 2.5 hours at 100° C. After cooling, the mixture is diluted with water (200 ml) and extracted with ethyl acetate (300 ml). The extract is washed successively with water, 0.1N hydrochloric acid and sodium bicarbonate solution, dried over anhydrous magnesium sulfate and evaporated in vacuo to give ethyl 7-(1-benzyloxycarbonyl-4-piperidyl)heptanoate (5 g) as an oil.

Workup

  1. waitthe stirring is continued for further 2.5 hours at 100° C
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate (300 ml)
  4. washThe extract is washed successively with water, 0.1N hydrochloric acid and sodium bicarbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-3b48a446545f4cb497a552b852c8b006
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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