Ammonia → HCID 70358231, compound

HRID 2165148Notes

Reaction equation

HRID 2165148 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:10][CH2:11][C:12]=1O)=[O:6])[CH3:3].[NH3:25]>O1CCOCC1>[ClH:1].[CH2:2]([O:4][C:5]([C:7]1[CH2:8][N:9]([CH2:14][C:15]2[C:18]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=3[CH:16]=2)[CH2:10][CH2:11][C:12]=1[NH2:25])=[O:6])[CH3:3].[ClH:1].[CH2:2]([O:4][C:5]([CH:7]1[C:12](=[NH:25])[CH2:11][CH2:10][NH:9][CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 70358074HCID 70358074, compound

Product 2

HCID 70358231HCID 70358231, compoundHCID 86744072HCID 86744072, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

3.5 g (10 mmol) of 4-hydroxy-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester hydrochloride in 50 ml of dioxan and 50 ml of 25% aqueous ammonia are heated in a bomb tube at 80° C., while stirring, for 48 hours. The reaction mixture is then extracted with trichloromethane; the extracts are washed with water, dried over sodium sulphate and concentrated under reduced pressure. The crude material is purified by chromatography, converted into the hydrochloride with hydrochloric acid and crystallised from methanol/diethyl ether. 4-amino-1-[(5-methoxybenzocyclobuten-1-yl)methyl]-1,2,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester hydrochloride alias 1-(5-methoxybenzocyclobuten-1-yl)methyl]-4-imino-piperidine-3-carboxylic acid ethyl ester hydrochloride of m.p. 184°-184.5° is obtained

Workup

  1. extractionThe reaction mixture is then extracted with trichloromethane
  2. washthe extracts are washed with water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customThe crude material is purified by chromatography
  6. customcrystallised from methanol/diethyl ether

Sources & evidence

ORD record
ord-fca835ef71824f1487d2e9f0a3678117
Source dataset
uspto-grants-1990_07
Patent number
US04939160

Reaction notes

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