Triethylamine → HCID 19780157, compound

HRID 2081558Notes

Reaction equation

HRID 2081558 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:7][N:6]([CH3:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([OH:15])=O)[C:4]=2[O:3]1.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH2:31][CH:32]1[CH:37]2[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]2)[CH2:33]1>C(OCC)(=O)C>[CH3:16][C:2]1([CH3:1])[CH2:7][N:6]([CH3:8])[C:5]2[CH:9]=[CH:10][CH:11]=[C:12]([C:13]([NH:31][CH:32]3[CH:37]4[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]4)[CH2:33]3)=[O:15])[C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 1232383-AminoquinuclidineHCID 19780143HCID 19780143, compound

Product 1

HCID 19780157HCID 19780157, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.0 g of 2,2,4-trimethyl-3,4-dihydro-2H-1,4-benzoxazine-8-carboxylic acid in 30 ml of ethyl acetate was added 1.2 ml of triethylamine, and 0.55 g of pivaloyl chloride was added dropwise thereto at -10° to -5° C. under cooling. After stirring for 15 minutes at the same temperature, 0.57 g of 3-aminoquinuclidine was added at -10° to -5° C. and the mixture was stirred at room temperature for an hour. The resultant mixture was washed with water, dried over magnesium sulfate and concentrated. The precipitated crystals were collected by filtration and recrystallized from a mixed solvent of isopropyl ether and ethanol to give 2,2,4-trimethyl-N-(3-quinuclidinyl)-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide as white crystals, melting at 114°-116° C.

Workup

  1. additionwas added dropwise
  2. temperatureat -10° to -5° C. under cooling
  3. additionwas added at -10° to -5° C.
  4. washThe resultant mixture was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. filtrationThe precipitated crystals were collected by filtration
  8. customrecrystallized from a mixed solvent of isopropyl ether and ethanol

Sources & evidence

ORD record
ord-3a29ed8be4f34ab6bfb400bc558979fa
Source dataset
uspto-grants-1993_02
Patent number
US05185333

Reaction notes

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