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

HRID 964976Notes

Reaction equation

HRID 964976 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 0C. 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-f70f104b7c2e47d48ad27a4f9374d200
Source dataset
uspto-grants-1998_06
Patent number
US05773444

Reaction notes

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