Sodium Hydroxide → HCID 21487853, compound

HRID 1414574Notes

Reaction equation

HRID 1414574 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][N:7]=[C:6]2[N:15]1[CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]1.[NH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.[BH4-].[Na+].[OH-].[Na+]>C1C=CC=CC=1.CCOCC.O.C(O)(=O)C.C(O)C>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][NH:22][CH:18]1[CH2:19][CH2:20][N:15]([C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH2:16][CH2:17]1

Participants

10

Reactant 4

HCID 14798Sodium HydroxideHCID 195092-PyridinemethanamineHCID 4311764Sodium borohydrideHCID 147388231-(6,7-Dimethoxy-4-quinazolinyl)-4-piperidinone

Product 1

HCID 21487853HCID 21487853, compoundYield 52.2%

Reagents, catalysts & solvents 5

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

1-(6,7-Dimethoxyquinazolin-4-yl)piperid-4-one (2.9g) (which may be prepared as in part A of Example 91, hereinafter), and 2-aminomethylpyridine (1.19g) were refluxed together for two hours in benzene (50 ml.) in a flask fitted with a Dean and Stark trap. Ethanol (50 ml.) was added to the cooled solution followed by the slow addition of sodium borohydride (0.76g) with stirring. On completion of the addition stirring as continued for two hours followed by the addition of excess acetic acid. The mixture was poured into water, basified with 5N sodium hydroxide and was extracted with chloroform. Evaporation of the chloroform layer gave a yellow oil which solidified on trituration with ether. Recrystallization from ethyl acetate gave 4-[4-(2-pyridylmethyl-amino)piperidino]-6,7-dimethoxyquinazoline (2 g) m.p. 151°-155° C.

Workup

  1. customfitted with a Dean and Stark trap
  2. additionOn completion of the addition
  3. stirringstirring
  4. extractionwas extracted with chloroform
  5. customEvaporation of the chloroform layer
  6. customgave a yellow oil which
  7. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-ef547666bb804d20b90fd13fe304d326
Source dataset
uspto-grants-1977_01
Patent number
US04001422

Reaction notes

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