Sulfuric Acid → HCID 18931229, compound

HRID 1599005Notes

Reaction equation

HRID 1599005 reaction equation
[NH2:1][C:2]1([C:26]#[N:27])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]2([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=3[O:24][CH3:25])OCC[O:13]2)[CH2:4][CH2:3]1.S(=O)(=O)(O)[OH:29]>O>[NH2:1][C:2]1([C:26]([NH2:27])=[O:29])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([C:17]2[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=2[O:24][CH3:25])=[O:13])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 18931291HCID 18931291, compound

Product 1

HCID 18931229HCID 18931229, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 4-amino-1-[5-(5-chloro-2-methoxyphenyl)-5,5-ethylenedioxypentyl]piperidine-4-carbonitrile (5.2 g, 13.1 mmol), prepared as in Example 20, water (1.6 mL) and sulfuric acid (41 mL) was warmed approximately 5 minutes on a steam bath and then cooled to 0° C. and diluted with water (150 mL). The mixture was washed with ethyl acetate (2×), cooled to 0° C. treated with potassium hydroxide, filtered, washed with chloroform and extracted with methylene chloride (4×). The combined extracts were dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate/hexane to give 4-amino-1-[5-(5-chloro-2-methoxyphenyl)-5-oxopentyl]piperidine-4-carboxamide (4.2 g, 11.4 mmol). Free base (135 mg, 0.367 mmol) was recrystallized from a solution of hydrogen chloride in ethanol to give 4-amino-1-[5-(5-chloro-2-methoxyphenyl)-5-oxo-pentyl]piperidine-4-carboxamide hydrochloride (65 mg, 0.16 mmol).

Workup

  1. temperaturewas warmed approximately 5 minutes on a steam bath
  2. washThe mixture was washed with ethyl acetate (2×)
  3. temperaturecooled to 0° C.
  4. additiontreated with potassium hydroxide
  5. filtrationfiltered
  6. washwashed with chloroform
  7. extractionextracted with methylene chloride (4×)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. concentrationconcentrated
  10. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-90b89051cce647b4aa995786f7d483bb
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

Loading…