Diisopropyl Ether → HCID 178451562, compound

HRID 1355580Notes

Reaction equation

HRID 1355580 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C@H:12]([C:14]2[NH:15][CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:18]=2)[NH2:13])=[CH:3]1.[C:25]([O:29][C:30]([N:32]1[CH2:37][CH2:36][C:35](=O)[CH2:34][CH2:33]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].C(OC(C)C)(C)C>C(O)(C)C>[C:19]1([C:17]2[N:18]=[C:14]([C@H:12]3[CH2:11][C:4]4[C:5]5[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=5)[NH:2][C:3]=4[C:35]4([CH2:36][CH2:37][N:32]([C:30]([O:29][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:31])[CH2:33][CH2:34]4)[NH:13]3)[NH:15][CH:16]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 178479294HCID 178479294, compound

Product 1

HCID 178451562HCID 178451562, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (1R)-2-(1H-indol-3-yl)-1-(4-phenyl-1H-imidazol-2-yl)-1-ethanamine hydrochloride (14 g, 35 mmol) in isopropanol (210 ml) was added 1-tert-butoxycarbonyl-4-piperidone (35 g, 170 mmol) and the mixture refluxed for about two hours. The solvent was evaporated under reduced pressure. Water (150 ml) was added to the residue followed by 10% NaHCO3 solution until neutral pH and extracted by ethyl acetate (4×50 ml). The combined organic extracts were washed with water (2×50 ml) and dried over MgSO4. The solvent was removed under reduced pressure to afford an oil which solidified on addition of diisopropyl ether (150 ml). The precipitate was collected by filtration, washed with diisopropyl ether and dried to afford 13.5 g of the desired product. Melting point: 118-120° C.

Workup

  1. temperaturethe mixture refluxed for about two hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionWater (150 ml) was added to the residue
  4. extractionextracted by ethyl acetate (4×50 ml)
  5. washThe combined organic extracts were washed with water (2×50 ml)
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customto afford an oil which
  9. filtrationThe precipitate was collected by filtration
  10. washwashed with diisopropyl ether
  11. customdried

Sources & evidence

ORD record
ord-571d1c2b625e479fbdac98b516dd6b76
Source dataset
uspto-grants-2003_07
Patent number
US06586445B1

Reaction notes

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