Ethanol → HCID 21413266, compound

HRID 1730346Notes

Reaction equation

HRID 1730346 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:14][CH2:13]1)([O-])=O.C(O)C.O>Cl>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][N:12]1[CH2:13][CH2:14][CH:15]([NH:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 702EthanolHCID 962WaterHCID 21413254HCID 21413254, compound

Product 1

HCID 21413266HCID 21413266, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 1-[2-(o-nitrophenyl)ethyl]-4-benzamidopiperidine (4.25 g.) inabsolute ethanol (150 ml.) was added over 50 minutes to stirred stannous chloride (10.82 g.) in concentrated hydrochloric acid (12 ml.). and water (7.5 ml.) at 60°-70° C. After addition, the mixture was stirred at this temperature for 4 hours before cooling and evaporating theethanol. Continuous extraction into chloroform of the neutralised (with 2N sodium hydroxide solution) aqueous fraction gave the title compound (1.65 g.). The aqueous layer after extraction was made alkaline with 2N sodium hydroxide solution and extracted with more chloroform to give a further batch of the title compound (2.36 g.). The total product was crystallised from ethanolic hydrogen chloride and ether to give the hydrochloride of the title compound (2.75 g.), m.p. 263.8° C. (Found: C, 60.3; H, 7.0; N, 10.5. C20H25N3O. 2HCl requires C, 60.6; H, 6.9; N, 10.60%).

Workup

  1. customat 60°-70° C
  2. additionAfter addition
  3. temperaturebefore cooling
  4. customevaporating theethanol
  5. extractionContinuous extraction into chloroform of the neutralised (with 2N sodium hydroxide solution) aqueous fraction

Sources & evidence

ORD record
ord-07b81cf82d464a2e8a2612ee03d87669
Source dataset
uspto-grants-1976_11
Patent number
US03992389

Reaction notes

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