4-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acid → HCID 10521792, compound

HRID 1756819Notes

Reaction equation

HRID 1756819 reaction equation
[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([OH:13])=O)=[CH:4][C:3]=1[Cl:14].[NH2:15][CH2:16][CH2:17][C:18]12[CH2:25][CH2:24][CH2:23][N:22]1[CH2:21][CH2:20][CH2:19]2>O1CCCC1>[NH2:1][C:2]1[C:10]2[CH2:9][CH2:8][O:7][C:6]=2[C:5]([C:11]([NH:15][CH2:16][CH2:17][C:18]23[CH2:19][CH2:20][CH2:21][N:22]2[CH2:23][CH2:24][CH2:25]3)=[O:13])=[CH:4][C:3]=1[Cl:14]

Participants

4

Reactant 2

HCID 106324014-Amino-5-chloro-2,3-dihydrobenzofuran-7-carboxylic acidHCID 107969772-(Hexahydro-1H-pyrrolizin-7a-yl)ethanamine

Product 1

HCID 10521792HCID 10521792, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Into an agitating solution of 4-amino-5-chloro-2,3-dihydrobenzo[b]furan-7-carboxylic acid (3.21 g) in absolute tetrahydrofuran (50 ml), was added little by little 1,1-carbonylimidazole (2.43 g) and after lapsed 1 hour, a solution of 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (2.31 g) in absolute tetrahydrofuran (2 ml) was added therein to reflux for 1 hour. After cooled, the solvent was distilled out in vacuo, a residue was dissolved into chloroform, washed with saturated sodium hydrogen carbonate solution and then water, and thereafter, the solvent was distilled out in vacuo. The resulting residue was refined by alumina column chromatography (developing solvent: chloroform) to afford 4.1 g of the titled compound.

Workup

  1. temperatureto reflux for 1 hour
  2. temperatureAfter cooled
  3. distillationthe solvent was distilled out in vacuo
  4. dissolutiona residue was dissolved into chloroform
  5. washwashed with saturated sodium hydrogen carbonate solution
  6. distillationwater, and thereafter, the solvent was distilled out in vacuo

Sources & evidence

ORD record
ord-78f3a3584fb04af6bdf6cb37fd3abae8
Source dataset
uspto-grants-1995_08
Patent number
US05442077

Reaction notes

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