Adipoyl chloride → n,n'-Bis-(1-indanyl)adipamide

HRID 650139

Reaction equation

HRID 650139 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[C:11](Cl)(=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16](Cl)=[O:17]>CCOCC>[CH:2]1([NH:1][C:11](=[O:19])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([NH:1][CH:2]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3]2)=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 61034Adipoyl chlorideHCID 123445(+-)-1-Aminoindan

Product 1

HCID 18627800n,n'-Bis-(1-indanyl)adipamideYield 60%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Racemic 1-aminoindan (5.7 g, 43 mmole) in ether (20 ml) stirred in ice, was treated dropwise with adipoyl chloride (1.83 g, 10 mmole) in ether (10 ml). After 30 min. the solid was filtered and slurried with water for 45 min. The insoluble solid was collected, air dried (2.82 g) and crystallized from HOAc/H2O, washed with acetic acid/water (1:1), ethanol and ether and then dried to give 2.26 g (60% title compound. Melting point: 227° C.

Workup

  1. filtrationAfter 30 min. the solid was filtered
  2. customThe insoluble solid was collected
  3. customair dried (2.82 g)
  4. customcrystallized from HOAc/H2O
  5. washwashed with acetic acid/water (1:1), ethanol and ether
  6. customdried

Sources & evidence

ORD record
ord-7ebf826dc868480c90044b2131fbd62f
Source dataset
uspto-grants-2001_08
Patent number
US06271263B1

Linked notes

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