Triethylamine → HCID 22890456, compound

HRID 896739Notes

Reaction equation

HRID 896739 reaction equation
[NH2:1][CH2:2][CH:3]([NH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([O:18][CH3:19])[CH:5]=1.Cl.NO.C([N:34](CC)CC)C>C(O)C.C(OCC)(=O)C.O>[NH2:1][CH2:2][CH:3]([NH:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]([NH2:34])=[NH:26])=[CH:23][CH:22]=1)[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([O:18][CH3:19])[CH:5]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 22890457HCID 22890457, compound

Product 1

HCID 22890456HCID 22890456, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
67.5 °C

Procedure

4-[2-Amino-1-(4-benzyloxy-3-methoxy-phenyl)-ethylamino]-benzonitrile D (300 mg, 0.8 mmoles) was dissolved in ethanol (3 ml) and hydroxylamine-hydrochloride (350 mg, 5 mmoles) and triethylamine (1 ml, 5.7 mmoles) were added. The reaction was heated to 65-70 degrees C. for 2 hours. The residue was taken up in ethyl acetate and water. The organic layer was separated, dried over anhydrous sodium sulfate and filtered. The solvent was removed in vacuo and replaced with 4 ml methanol with 0.5 ml acetic acid. Raney nickel (ca. 300 ul suspension in sodium hydroxide, Aldrich) was added and the reaction placed under a hydrogen atmosphere. The reaction was stirred vigorously for 3 hours, the catalyst filtered off and the solvent removed in vacuo. The crude product was purified by flash chromatography on silica gel (ethyl acetate:acetone:methanol:ammonia, 2:1:1:0.05) to yield 160 mgs of 4-[2-Amino-1-(4-benzyloxy-3-methoxy-phenyl)-ethylamino]-benzamidine E. MS (M+H)=391.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed in vacuo
  5. additionRaney nickel (ca. 300 ul suspension in sodium hydroxide, Aldrich) was added
  6. filtrationthe catalyst filtered off
  7. customthe solvent removed in vacuo
  8. customThe crude product was purified by flash chromatography on silica gel (ethyl acetate:acetone:methanol:ammonia, 2:1:1:0.05)

Sources & evidence

ORD record
ord-8368306a49f941338dea3fc7ec9d4a0a
Source dataset
uspto-grants-2005_07
Patent number
US06919369B2

Reaction notes

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