Hydrochloric Acid → 1,2,3,6-Tetrahydro-4-[2-(2-thienyl)ethynyl]pyridine

HRID 355390Notes

Reaction equation

HRID 355390 reaction equation
C(OC([N:8]1[CH2:13][CH:12]=[C:11]([C:14]#[C:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)C.O>[S:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[C:15]#[C:14][C:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 18942191HCID 18942191, compound

Product 1

HCID 189421761,2,3,6-Tetrahydro-4-[2-(2-thienyl)ethynyl]pyridineYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-tert-butoxycarbonyl-4-(2-thienyl)ethynyl-1,2,3,6-tetrahydropyridine (530 mg, 1.8 mmol) (prepared in a manner analogous to Example 1) in diethyl ether (10 ml) at room temperature under a nitrogen atmosphere was treated with excess ethereal hydrogen chloride. Following a 3 hour stir at room temperature the dark mixture was diluted with water and extracted with diethyl ether (2×30 ml). The aqueous phase was made basic with potassium carbonate solution (sat.) and extracted with diethyl ether (3×50 ml). The extracts were dried (K2CO3) and evaporated in vacuo to give the title compound as a brown oil (267 mg, 77%); δH (CDCl3) 2.24-2.29 (2H, m, tetrahydropyridinyl CH2), 3.00 (2H, J 5.7 Hz, tetrahydropyridinyl CH2), 3.45-3.47 (2H, m, tetrahydropyridinyl CH2), 6.17-6.19 (1H, m, tetrahydropyridinyl CH), 6.94-6.97 (1H, m, ArH), 7.16-7.17 (1H, m, ArH) and 7.22-7.26 (1H, m, ArH).

Workup

  1. extractionextracted with diethyl ether (2×30 ml)
  2. extractionextracted with diethyl ether (3×50 ml)
  3. dry with materialThe extracts were dried (K2CO3)
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-13bb71ef9b1b4085a94702172d49ed15
Source dataset
uspto-grants-1998_11
Patent number
US05830901

Reaction notes

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