3-Azabicyclo[3.2.2]nonane → HCID 86755513, compound

HRID 2288198Notes

Reaction equation

HRID 2288198 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]1[CH:4]=[C:5]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=O)[CH2:10][C@H:9]1[CH2:18][C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[NH:21][CH:20]=1)=[O:7].[CH:37]12[CH2:45][CH2:44][CH:41]([CH2:42][CH2:43]1)[CH2:40][NH:39][CH2:38]2.[ClH:46].CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[ClH:46].[CH:37]12[CH2:45][CH2:44][CH:41]([CH2:42][CH2:43]1)[CH2:40][N:39]([C:15]([CH2:14][N:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:4]=[C:3]([C:2]([F:36])([F:35])[F:1])[CH:30]=[C:29]([C:31]([F:32])([F:34])[F:33])[CH:28]=3)[C@H:9]([CH2:18][C:19]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[CH2:10]1)=[O:17])[CH2:38]2

Participants

7

Reactant 5

HCID 92403-Azabicyclo[3.2.2]nonaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10962313HCID 10962313, compound

Product 1

HCID 86755513HCID 86755513, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(carboxymethyl)-2-(1H-indol-3-ylmethyl)piperazine (0.2 g) and 3-azabicyclo[3.2.2]nonane (0.05 g) in dry N,N-dimethylformamide (2 ml) were added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.082 g) and 1-hydroxybenzotriazole (0.058 g) at room temperature. After 6 hours, the reaction mixture was poured into aqueous sodium bicarbonate solution (20 ml) and the resulting precipitate was collected by filtration. The crude product obtained was purified by column chromatography on silica gel using toluene-ethyl acetate (1:2) as an eluent and treated with 17.6% hydrogen chloride in ethanol solution to give (2R)-4-[(3-azabicyclo[3.2.2]non-3-yl) carbonylmethyl]-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine hydrochloride (0.2 g) as a white powder.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. customThe crude product obtained
  3. customwas purified by column chromatography on silica gel
  4. additiontreated with 17.6% hydrogen chloride in ethanol solution

Sources & evidence

ORD record
ord-48e36cef89234273b78d74e0316a9db7
Source dataset
uspto-grants-2000_07
Patent number
US06087357

Reaction notes

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