Hydrochloric Acid → HCID 23000931, compound

HRID 397746Notes

Reaction equation

HRID 397746 reaction equation
[CH2:1]([N:7]1[CH2:12][CH2:11][C:10]([CH3:33])([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N:19]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)[CH2:9][CH2:8]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl>O1CCCC1>[NH2:19][C:15]1[CH:14]=[C:13]([C:10]2([CH3:33])[CH2:11][CH2:12][N:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:8][CH2:9]2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 23000998HCID 23000998, compound

Product 1

HCID 23000931HCID 23000931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-hexyl-4-methyl-4-(3-diphenylmethylideneaminophenyl)piperidine (Preparation 55, 112 mg, 0.26 mmol) in tetrahydrofuran (4 ml) was added 2N aqueous hydrochloric acid (1 ml) and the mixture was stirred at room temperature for 30 min. The mixture was concentrated in vacuo, 2N aqueous hydrochloric acid (3 ml) was added and the aqueous phase was extracted with hexane:ethyl acetate (2:1, 5 ml). The aqueous layer was then basified with 2N aqueous sodium hydroxide solution and extracted with dichloromethane (3×10 ml). The combined extracts of the basic aqueous layer were dried (MgSO4), filtered and concentrated in vacuo to give the title compound which was used without further purification (70 mg, 99% crude yield).

Workup

  1. concentrationThe mixture was concentrated in vacuo, 2N aqueous hydrochloric acid (3 ml)
  2. additionwas added
  3. extractionthe aqueous phase was extracted with hexane:ethyl acetate (2:1, 5 ml)
  4. extractionextracted with dichloromethane (3×10 ml)
  5. dry with materialThe combined extracts of the basic aqueous layer were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-844f90e835b84c02b26d794b690a2105
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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