Hydrochloric Acid → 5-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamine

HRID 1015329Notes

Reaction equation

HRID 1015329 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18]([NH2:27])=[N:19][C:20]([NH2:26])=[N:21]3)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[C:18]([NH2:27])=[N:19][C:20]([NH2:26])=[N:21]3)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66924145HCID 66924145, compound

Product 1

HCID 575765655-(Piperidin-4-ylmethoxy)quinazoline-2,4-diamineYield 75%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4-(2,4-Diamino-quinazolin-5-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (16.4 g; 44.0 mmol) was suspended in 80 mL of dioxane and 4M HCl in dioxane (176 mL, 176 mmol) was added changing the mixture from homogenous to heterogenous. After 5 hrs of stirring at room temperature, solids were filtered off and rinsed once with ether. Solids were triturated with 1 N NaOH for 30 minutes. Solids were collected by filtration and dried to yield 5-(piperidin-4-ylmethoxy)quinazoline-2,4-diamine. (9.05 g; 75% yield).

Workup

  1. filtrationsolids were filtered off
  2. washrinsed once with ether
  3. customSolids were triturated with 1 N NaOH for 30 minutes
  4. filtrationSolids were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-17c112a74ea3436180d65fcb757505e0
Source dataset
uspto-grants-2011_07
Patent number
US07985755B2

Reaction notes

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