Sodium Hydroxide → HCID 18929550, compound

HRID 1598539Notes

Reaction equation

HRID 1598539 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.Cl[C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[C:12]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[N:11]=1.CCN(C(C)C)C(C)C.[OH-].[Na+]>C(#N)CCC.C(OCC)(=O)C>[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]([N:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[N:11]=2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 235274-(Aminomethyl)piperidineHCID 81531DiisopropylethylamineHCID 10933458HCID 10933458, compound

Product 1

HCID 18929550HCID 18929550, compound

Reagents, catalysts & solvents 2

HCID 8008ButyronitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(aminomethyl)-piperidine (1.2 g, 11 mmol), 4-chloro-2-diethylaminoquinazoline (1.2 g, 5.1 mmol) and Hunig's base (2.8 ml, 16 mmol) in 10 ml of butyronitrile was reacted for 12 hours at 100° C. After cooling, ethyl acetate (50 ml) and 50 ml of sodium hydroxide (10%) were added. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×25 ml). The combined organic phases were dried (Na2SO4), concentrated on a rotary evaporator and purified by chromatography on silica gel (eluent: methylene chloride/ethanol/ammonia, 50/10/1) to give the free base as a solid.

Workup

  1. customwas reacted for 12 hours at 100° C
  2. temperatureAfter cooling
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (2×25 ml)
  5. dry with materialThe combined organic phases were dried (Na2SO4)
  6. concentrationconcentrated on a rotary evaporator
  7. custompurified by chromatography on silica gel (eluent: methylene chloride/ethanol/ammonia, 50/10/1)

Sources & evidence

ORD record
ord-e4d8d88746374fd59528f6d8638fa3ae
Source dataset
uspto-grants-1998_04
Patent number
US05739127

Reaction notes

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