Hydrochloric Acid → Lamtidine

HRID 2058724Notes

Reaction equation

HRID 2058724 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([N:21]=[C:22]([N:25]([CH3:34])[N:26]=CC1C=CC=CC=1)SC)#[N:20].Cl>CC(C)=O>[CH3:34][N:25]1[C:22]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)=[N:21][C:19]([NH2:20])=[N:26]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 54323404methyl N-cyano-1-methyl-2-(phenylmethylene)-hydrazinecarboximidothioate

Product 1

HCID 71988LamtidineYield 28.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[3-[1-Piperidinylmethyl]phenoxy]propanamine (2.48 g) and N-cyano-1-methyl-2-(phenylmethylene)hydrazine carboximidothioic acid, methyl ester (2.32 g) were heated at 70° under water-pump vacuum for 4 hr. Acetone was added and the solution was treated with dilute hydrochloric acid for 1 hr, washed with ether, basified and extracted with ethyl acetate. Evaporation of the ethyl acetate extracts gave an oil which crystallised from toluene/ether to give the title compound as a white solid (0.98 g) m.p. 94°-5°. TLC silica, methanol/0.88 ammonia 80:1, Rf 0.5.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. customEvaporation of the ethyl acetate extracts
  4. customgave an oil which
  5. customcrystallised from toluene/ether

Sources & evidence

ORD record
ord-2994e54391aa44929a578e03540b22b5
Source dataset
uspto-grants-1982_03
Patent number
US04318913

Reaction notes

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