Hydrochloric Acid → 4-[cis-3,5-Dimethyl-1-piperazinyl]-2-pyridinamine

HRID 2234986Notes

Reaction equation

HRID 2234986 reaction equation
[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:10]=2)[CH2:3]1.Cl>O1CCCC1.O>[CH3:1][C@H:2]1[NH:7][C@@H:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 589881374-[cis-3,5-Dimethyl-1-piperazinyl]-N-(diphenylmethylidene)-2-pyridinamine

Product 1

HCID 589881294-[cis-3,5-Dimethyl-1-piperazinyl]-2-pyridinamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[cis-3,5-dimethyl-1-piperazinyl]-N-(diphenylmethylidene)-2-pyridinamine (D20) (650 mg, 1.76 mmol) in tetrahydrofuran (5 ml) was treated with 1.0M hydrochloric acid (5 ml) and the mixture stirred at room temperature for 1 hour. The mixture was diluted with water and washed with diethyl ether. The aqueous phase was basified with 50% aq. sodium hydroxide then saturated with sodium chloride. The mixture was extracted with ethyl acetate (×2). The combined extracts were dried and evaporated to give the title compound (D21). 1H NMR CDCl3 ppm δ (6H, d), 2.33-0.238 (2H, m), 2.91-2.96 (2H, m), 3.58-3.62 (2H, m), 5.85 (1H, s), 6.18-6.20 (1H, m), 7.78-8.00 (1H, d).

Workup

  1. washwashed with diethyl ether
  2. extractionThe mixture was extracted with ethyl acetate (×2)
  3. customThe combined extracts were dried
  4. customevaporated

Sources & evidence

ORD record
ord-e3e23f8a0b4d4025bb2971452f7fd5c5
Source dataset
uspto-grants-2010_05
Patent number
US07713978B2

Reaction notes

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