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

HRID 1791701Notes

Reaction equation

HRID 1791701 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-8e3da567cf4548409d45d737a189f0dc
Source dataset
uspto-grants-2006_07
Patent number
US07074800B1

Reaction notes

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