Sulfuric Acid → 6'-Bromo-1'H-spiro[piperidine-4,2'-quinazolin]-4'(3'H)-one

HRID 1639542Notes

Reaction equation

HRID 1639542 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].C([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)(OC(C)(C)C)=O.S(=O)(=O)(O)O>C(O)(=O)C.C(OCC)C>[Br:11][C:8]1[CH:7]=[C:3]2[C:2](=[CH:10][CH:9]=1)[NH:1][C:22]1([CH2:23][CH2:24][NH:19][CH2:20][CH2:21]1)[NH:6][C:4]2=[O:5]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 50192712-Amino-5-bromobenzamide

Product 1

HCID 247151026'-Bromo-1'H-spiro[piperidine-4,2'-quinazolin]-4'(3'H)-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 33 mg (0.15 mmol) of 2-amino-5-bromobenzamide and 30 mg (0.15 mmol) of 1-Boc-4-piperidone in 400 μL of acetic acid containing 10 μL of sulfuric acid is stirred overnight at room temperature. The reaction mixture is diluted with diethyl ether. The yellow precipitate is collected by filtration, washed with excess ether, and dried under vacuum to give 55 mg (0.15 mmol) of the acetic acid salt of 6′-bromospiro-[piperidine-4,2′(1′H)-quinazolin]-4′-(3′H)-one. MS m/z: 297.0 (M+H)+, 319.0 (M+Na)+.

Workup

  1. filtrationThe yellow precipitate is collected by filtration
  2. washwashed with excess ether
  3. customdried under vacuum

Sources & evidence

ORD record
ord-9feaee248f394163a1848660df0c3a9b
Source dataset
uspto-grants-2012_02
Patent number
US08110570B2

Reaction notes

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