Triethylamine → HCID 20058356, compound

HRID 2050481Notes

Reaction equation

HRID 2050481 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH2:11][C:12]([OH:14])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:29][CH:30]1[CH:35]2[CH2:36][CH2:37][N:32]([CH2:33][CH2:34]2)[CH2:31]1.C(N(CC)CC)C>C1COCC1.[Cl-].[Na+].O>[N:32]12[CH2:37][CH2:36][CH:35]([CH2:34][CH2:33]1)[CH:30]([NH:29][C:12](=[O:14])[CH2:11][C:3]1[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:31]2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 8259602-(1-Methyl-1H-indol-2-yl)acetic acid

Product 1

HCID 20058356HCID 20058356, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-methyl-1H-indole-2-acetic acid (830 mg) in THF (20 ml) was added 1,1'-carbonyldiimidazole (782 mg), and the mixture was stirred for 1 h. 3-Aminoquinuclidine dihydrochloride (960 mg) was then added, followed by triethylamine (2.34 g), and the mixture was stirred overnight at room temperature. The mixture was then poured into brine (200 ml) and extracted with ethyl acetate (2x200 ml). The combined, dried organic extracts were evaporated in vacuo to give a solid which was purified by FCC eluting with System A (50:8:1) to give the title compound (1.30 g), m.p. 185-187°.

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. extractionextracted with ethyl acetate (2x200 ml)
  3. customdried organic extracts were evaporated in vacuo
  4. customto give a solid which
  5. customwas purified by FCC
  6. washeluting with System A (50:8:1)

Sources & evidence

ORD record
ord-1b8e2d40bada4c95948a914b9d41443b
Source dataset
uspto-grants-1991_05
Patent number
US05013733

Reaction notes

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