Hydrochloric Acid → HCID 178468491, compound

HRID 1879922Notes

Reaction equation

HRID 1879922 reaction equation
Cl[C:2]1[N:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.[CH2:17]([O:19][C:20]([C:22]1([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)=[O:21])[CH3:18].Cl.CCN(C(C)C)C(C)C>C(O)C>[CH2:17]([O:19][C:20]([C:22]1([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:23][CH2:24][N:25]([C:2]2[N:11]=[C:10]([OH:12])[C:9]3[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=3)[N:3]=2)[CH2:26][CH2:27]1)=[O:21])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 53297794Ethyl 4-benzylpiperidine-4-carboxylateHCID 178486816HCID 178486816, compound

Product 1

HCID 178468491HCID 178468491, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.2 g (5 mmol) 2-Chloro-6,7-dimethoxy-quinazolin-4-ol (commercially available), 2.26 g (8 mmol) 4-Benzyl-piperidine-4-carboxylic acid ethyl ester; hydrochloride and 1.93 g (15 mmol) DIPEA in 80 mL ethanol was heated to reflux for 62 h. The mixture was concentrated, the precipitate filtered off and washed with ethanol and diethyl ether. The residue was dried. 1.9 g (87%) of the title compound was isolated as white solid. MS (m/e): 452.2 (MH+).

Workup

  1. temperatureto reflux for 62 h
  2. concentrationThe mixture was concentrated
  3. filtrationthe precipitate filtered off
  4. washwashed with ethanol and diethyl ether
  5. customThe residue was dried

Sources & evidence

ORD record
ord-aa5c635bbc684f72bb11a0fa9105a0d8
Source dataset
uspto-grants-2012_11
Patent number
US08318749B2

Reaction notes

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