Hydrochloric Acid → 6-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine

HRID 53645

Reaction equation

HRID 53645 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][CH2:12][CH2:13][N:14]2[CH2:19][CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[N:8][CH:9]=1)([O-])=O.Cl>C(O)C.O>[C:20]1([C:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][C:11]#[C:10][C:7]3[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=3)[CH2:15][CH:16]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 106880901,2,3,6-Tetrahydro-1-[4-(5-nitro-2-pyridinyl)-3-butynyl]-4-phenylpyridine

Product 1

HCID 100863486-[4-(3,6-Dihydro-4-phenyl-1(2H)-pyridinyl)-1-butynyl]-3-pyridinamine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1,2,3,6-tetrahydro-1-[4-(5-nitro-2-pyridinyl)-3-butynyl]-4-phenylpyridine (Example 9) (2.0 g, 0.006 mol), reduced iron (3.1 g), and 0.10 mL of concentrated hydrochloric acid in 30 mL of 95% ethanol and 10 mL of water is heated at 80° C. with vigorous stirring for 30 minutes. The hot solution is filtered through diatomaceous earth (Celite), and the filter cake is washed with 300 mL of hot ethanol. The solvent is removed under reduced pressure, and the residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate. The aqueous layer is extracted with dichloromethane and the combined organic layers are washed with water and dried (sodium sulfate), and the solvent is removed in vacuo. The residue is chromatographed (silica gel, 2% methanol/98% dichloromethane) to give the title compound, containing 0.3 mol of water; mp 135.5°-137° C.

Workup

  1. filtrationThe hot solution is filtered through diatomaceous earth (Celite)
  2. washthe filter cake is washed with 300 mL of hot ethanol
  3. customThe solvent is removed under reduced pressure
  4. customthe residue is partitioned between 50 mL of dichloromethane and 50 mL of saturated aqueous sodium bicarbonate
  5. extractionThe aqueous layer is extracted with dichloromethane
  6. washthe combined organic layers are washed with water
  7. dry with materialdried (sodium sulfate)
  8. customthe solvent is removed in vacuo
  9. customThe residue is chromatographed (silica gel, 2% methanol/98% dichloromethane)

Sources & evidence

ORD record
ord-46040e44c1e043e49a0afeccbb90667f
Source dataset
uspto-grants-1997_04
Patent number
US05620988

Linked notes

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