Sodium Bicarbonate → 4-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline

HRID 454175Notes

Reaction equation

HRID 454175 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 220308104-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline hydrochloride

Product 1

HCID 110885414-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline hydrochloride was suspended in methylene chloride (10 ml) and saturated aqueous sodium hydrogen carbonate solution (5 ml) then stirred vigorously for 10 minutes at ambient temperature. The layers were separated and the organic layer dried (MgSO4) then evaporated to give a white solid. This solid was triturated with methanol (2.5 ml), the resulting solid filtered off, washed with cold methanol and dried to give 4-chloro-6-methoxy-7-(2-piperidinoethoxy)quinazoline (0.36 g).

Workup

  1. customThe layers were separated
  2. dry with materialthe organic layer dried (MgSO4)
  3. customthen evaporated
  4. customto give a white solid
  5. customThis solid was triturated with methanol (2.5 ml)
  6. filtrationthe resulting solid filtered off
  7. washwashed with cold methanol
  8. customdried

Sources & evidence

ORD record
ord-7531cebbcd154483ab7583a853d19014
Source dataset
uspto-grants-2013_07
Patent number
US08492560B2

Reaction notes

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