Potassium Carbonate → tert-Butyl 1-(4-bromophthalazin-1-yl)piperidin-4-yl(methyl)carbamate

HRID 1466219Notes

Reaction equation

HRID 1466219 reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Br:12])=[N:4][N:3]=1.CN1CCCC1=O.C(=O)([O-])[O-].[K+].[K+].[C:26]([O:30][C:31](=[O:40])[N:32]([CH3:39])[CH:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27]>O>[Br:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:36]2[CH2:35][CH2:34][CH:33]([N:32]([CH3:39])[C:31](=[O:40])[O:30][C:26]([CH3:27])([CH3:28])[CH3:29])[CH2:38][CH2:37]2)=[N:3][N:4]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 596273921,4-Dibromophthalazine

Product 1

HCID 59627406tert-Butyl 1-(4-bromophthalazin-1-yl)piperidin-4-yl(methyl)carbamateYield 95.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Combine 1,4-dibromophthalazine (0.70 g, 2.38 mmol), N-methylpyrrolidone (7.0 mL), potassium carbonate (395 mg, 2.86 mmol), and methyl-piperidin-4-yl-carbamic acid tert-butyl ester (532 mg, 2.38 mmol). Heat at 80° C. overnight. Cool and pour into water. Collect the solid and dry in a vacuum oven at ambient temperature overnight to obtain the final product (0.96 g, 95%). ES/MS m/z (81Br) 421.0 (M+1).

Workup

  1. temperatureCool
  2. customCollect the solid
  3. customdry in a vacuum oven at ambient temperature overnight

Sources & evidence

ORD record
ord-7d52725b596e4c58a46c841413fe4463
Source dataset
uspto-grants-2015_04
Patent number
US09000023B2

Reaction notes

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