Indan-5-amine → HCID 10198118, compound

HRID 1836273Notes

Reaction equation

HRID 1836273 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH2:6][CH2:5]2.[N:11]1(S(O)(=O)=O)[CH2:15][CH2:14][N:13]=[CH:12]1>C(O)C(C)C.ClCCl>[CH2:7]1[C:8]2[C:4](=[CH:3][C:2]([NH:1][C:12]3[NH:13][CH2:14][CH2:15][N:11]=3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

5

Reactant 2

HCID 90496Indan-5-amineHCID 21943817HCID 21943817, compound

Product 1

HCID 10198118HCID 10198118, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6560IsobutanolSolvent

Procedure

A mixture of 5-aminoindan (200 mg, 1.50 mmol) and 2-imidazolinesulfonic acid (450 mg, 3.00 mmol) in isobutyl alcohol (5 mL) was heated at reflux for 3 h and then stirred overnight. The solvent was removed to give a dark oil. It was flash chromatographed over silica gel (EtOAc:MeOH:Et3N=6:2:1) to afford a yellow solid. The solid was redissolved in dichloromethane, and washed with saturated aqueous Na2CO3. The organic layer was dried and concentrated to give yellow crystals (220 mg, 73% yield): mp 41-42° C.; EIMS m/z=201 (M+). Anal. Calcd. for C12H15N3 4/5H2O: C, 66.82; H, 7.74; N, 19.48. Found: C, 66.77; H, 7.31; N, 19.24.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. customThe solvent was removed
  4. customto give a dark oil
  5. customchromatographed over silica gel (EtOAc:MeOH:Et3N=6:2:1)
  6. customto afford a yellow solid
  7. washwashed with saturated aqueous Na2CO3
  8. customThe organic layer was dried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b73badc0ea3f4f04adb194b49cc87a8e
Source dataset
uspto-grants-2004_08
Patent number
US06777426B2

Reaction notes

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