3-amino-N-ethylpiperidine → (1-Ethyl-piperidin-3-yl)-(6-iodo-2-trichloromethyl-quinazolin-4-yl)-amine, monohydrochloride

HRID 2257510Notes

Reaction equation

HRID 2257510 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[N:6]=[C:5]2Cl.[NH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH3:25])[CH2:19]1>CCOCC>[ClH:13].[CH2:24]([N:20]1[CH2:21][CH2:22][CH2:23][CH:18]([NH:17][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=3)[N:8]=[C:7]([C:12]([Cl:15])([Cl:14])[Cl:13])[N:6]=2)[CH2:19]1)[CH3:25]

Participants

4

Reactant 2

HCID 980943-amino-N-ethylpiperidineHCID 6329086-Iodo-4-chloro-2-trichloromethyl quinazolin

Product 1

HCID 131720118(1-Ethyl-piperidin-3-yl)-(6-iodo-2-trichloromethyl-quinazolin-4-yl)-amine, monohydrochloride

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

6-iodo-4-chloro-2-trichloromethyl-quinazolin (8.14 g, 20 mmol) was dissolved in ether (anhydrous 200 mL) under stirring at rt. To this solution 3-amino-1-ethyl-piperidine (2.56 g, 20 mmol) in ether (anhydrous 30 mL) was added at 0° C. The reaction mixture was allowed to warm to rt overnight. Buff colored solid separated which was filtered, washed with ether (200 mL) and air dried. Crude yield: 5.1 g. The crude material was suspended in MeOH and stirred vigorously for 0.5 h and filtered. The solid was dried in vacuo (0.01 mm). Yield: 3.72 g, (34.7%). Mp 265°-266° C.

Workup

  1. temperatureto warm to rt overnight
  2. customseparated which
  3. filtrationwas filtered
  4. washwashed with ether (200 mL) and air
  5. customdried
  6. stirringstirred vigorously for 0.5 h
  7. filtrationfiltered
  8. customThe solid was dried in vacuo (0.01 mm)

Sources & evidence

ORD record
ord-45e6251736204cf6acce527709e0c3ea
Source dataset
uspto-grants-1997_08
Patent number
US05658902

Reaction notes

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