Isatoic Anhydride → HCID 13060622, compound

HRID 1782703Notes

Reaction equation

HRID 1782703 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:15]12[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=1)[NH:20]C(=O)O[C:16]2=[O:17]>O1CCCC1.C(O)C>[NH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:15]=1[C:16]([NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][CH2:3]1)=[O:17]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 4158521-Benzyl-4-piperidylamine

Product 1

HCID 13060622HCID 13060622, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cold solution of 28 ml (134 mmol) of 4-amino-1-(phenylmethyl)piperidine in 200 ml of tetrahydrofuran were added, batchwise, 21.9 g (134 mmol) of isatoic acid anhydride. The resulting suspension was stirred for 2½ hours at room temperature and 2½ hours at reflux temperature, then freed from solvent. The residue was dissolved in 100 ml of hot ethanol, the resulting solution was filtered whilst hot after the addition of 5 g of activated charcoal. The crystal mass precipitated after cooling was suction filtered, washed with diisopropylether and dried in vacuo at 50° C. 28.3 g of colourless crystals were obtained. A further 5.1 g of a product of the same quality were isolated from the combined mother liquors. Total yield: 33.4 g (80.6% of theory).

Workup

  1. temperatureat reflux temperature
  2. filtrationthe resulting solution was filtered whilst
  3. additionhot after the addition of 5 g of activated charcoal
  4. customThe crystal mass precipitated
  5. temperatureafter cooling
  6. washwashed with diisopropylether
  7. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-6db817171436441985f094ec712656cc
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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