Hydrochloric Acid → HCID 19019103, compound

HRID 1110104Notes

Reaction equation

HRID 1110104 reaction equation
[CH3:1][C:2]1[S:6][CH:5]=[C:4]2[C:7]([NH:9][C:10]3[C:15]([N:16]([C:17]([CH2:19][N:20]4[CH2:25][CH2:24][N:23](C)[CH2:22][CH2:21]4)=[O:18])[C:3]=12)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:8].Cl.Cl.ClC(OC(Cl)C)=O.C(N(C(C)C)CC)(C)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.CO.CCOCC>[CH3:1][C:2]1[S:6][CH:5]=[C:4]2[C:7](=[O:8])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[N:16]([C:17](=[O:18])[CH2:19][N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:3]=12

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 81531DiisopropylethylamineHCID 5213051-Chloroethyl chloroformateHCID 6419995Telenzepine dihydrochloride

Product 1

HCID 19019103HCID 19019103, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

Telenzepine dihydrochloride (0.10 g, 0.23 mmol), α-chloroethyl chloroformate (0.2mL), and N,N,N-diisopropylethylamine (0.3 mL) were suspended in 100 mL anhydrous CHCl3 and the mixture was refluxed for 2 h, treated with an additional 0.1 mL of diisopropylethylamine, and heated 10 min. The CHCl3 was removed in vacuo and the solid (consisting mainly of the N-(α-chloroethyloxycarbonyl) intermediate which was not isolated) was dissolved in 7 mL of methanol and sufficient 1M HCl in ether to lower the pH to 0-1. The solution was refluxed for another 0.5 h and immediately basified with aqueous sodium carbonate and washed with ether. The aqueous layer was saturated with NaCl and extracted into CHCl3 to yield 40 mg (50%) of 38. 1H NMR (CDCl3) spectrum showed a characteristic singlet for the thiophene CH3 at δ 2.43 ppm; MS (Cl/NH3) m/e 353 (MH30, base).

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. temperatureheated 10 min
  3. customThe CHCl3 was removed in vacuo
  4. customwas not isolated)
  5. temperatureThe solution was refluxed for another 0.5 h
  6. washwashed with ether
  7. extractionextracted into CHCl3

Sources & evidence

ORD record
ord-d93cb732af034d36be6046bcb343139f
Source dataset
uspto-grants-1994_06
Patent number
US05324832

Reaction notes

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