HCID 54401137, compound → HCID 53673610, compound

HRID 1684759Notes

Reaction equation

HRID 1684759 reaction equation
[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12](=O)[NH:13]N2CCCCC2)=[CH:6][C:5]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27]>O1CCCC1>[CH3:1][O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][N:13]2[CH2:8][CH2:9][CH2:4][CH2:5][CH2:6]2)=[CH:6][C:5]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH3:27]

Participants

3

Reactant 1

HCID 54401137HCID 54401137, compound

Product 1

HCID 53673610HCID 53673610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-(4-methoxybutoxy)-4-(piperidin-1-ylcarbamoylmethoxy)-benzoic acid methyl ester (2.29 g) in tetrahydrofuran (10 ml) is added dropwise at 0°-5° C. over a period of 15 minutes to a 1M borane THF complex solution in tetrahydrofuran (10.0 ml). The mixture is then heated to reflux temperature and stirred for 4 hours. A further 2.0 ml of a 1M borane THF complex solution are added. After one hour under reflux, the mixture is allowed to cool, the solvent is removed, and anhydrous methanol (0.97 ml) and 3.75N hydrochloric acid solution in diethyl ether (1.61 ml) are added to the residue. After stirring overnight at room temperature, the mixture is concentrated and the crude product is purified by FC (eluant gradient from P to N). 2-(4-Methoxybutoxy)-4-(piperidin-1-ylethoxy)-benzoic acid methyl ester, Rf (L)=0.38, is obtained in the form of a brown oil (1.39 g).

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux temperature
  3. additionA further 2.0 ml of a 1M borane THF complex solution are added
  4. temperatureAfter one hour under reflux
  5. temperatureto cool
  6. customthe solvent is removed
  7. additionanhydrous methanol (0.97 ml) and 3.75N hydrochloric acid solution in diethyl ether (1.61 ml) are added to the residue
  8. stirringAfter stirring overnight at room temperature
  9. concentrationthe mixture is concentrated
  10. customthe crude product is purified by FC (eluant gradient from P to N)

Sources & evidence

ORD record
ord-fe6c0add1733482c96c40746cb25c51d
Source dataset
uspto-grants-1997_06
Patent number
US05641778

Reaction notes

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