Ammonium nitrate → HCID 22127973, compound

HRID 1858781Notes

Reaction equation

HRID 1858781 reaction equation
[N+]([O-])([O-])=O.[NH4+].C[O:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18]C)=[CH:10][C:9]=1[CH2:20][O:21][CH:22]1[CH:27]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][O:37][CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[CH:30][CH:29]=2)[CH2:26][CH2:25][NH:24][CH2:23]1>O.C(#N)C>[CH2:38]([O:37][CH2:36][CH2:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH:27]2[CH2:26][CH2:25][NH:24][CH2:23][CH:22]2[O:21][CH2:20][C:9]2[C:8](=[O:7])[C:17]3[C:12]([C:11](=[O:18])[CH:10]=2)=[CH:13][CH:14]=[CH:15][CH:16]=3)=[CH:33][CH:32]=1)[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

5

Reactant 2

HCID 22985Ammonium nitrateHCID 22126946HCID 22126946, compound

Product 1

HCID 22127973HCID 22127973, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 240 mg of Cer(IV) ammonium nitrate in 1 ml of water was added dropwise at room temperature to a solution of 118 mg of (3RS,4RS)-3-(1,4-dimethoxy-naphthalen-2-ylmethoxy)-4-[4-(2-phenethyloxy-ethoxy)-phenyl]-piperidine in 10 ml of acetonitrile. The reaction solution was stirred at room temperature for 15 minutes and subsequently evaporated under reduced pressure. The residue was partitioned between methylene chloride and water, the organic phase was dried and evaporated under reduced pressure. For purification, the crude product was chromatographed on silica gel using a 9:1 mixture of methylene chloride and methanol as the eluent. There were obtained 95 mg (85% of theory) of (3RS,4RS)-2-[4-[4-(2-phenethyloxy-ethoxy)-phenyl]-piperidin-3-yloxymethyl]-[1,4]naphthoquinone as a red solid; MS: 512 (M+H)+.

Workup

  1. customsubsequently evaporated under reduced pressure
  2. customThe residue was partitioned between methylene chloride and water
  3. customthe organic phase was dried
  4. customevaporated under reduced pressure
  5. customFor purification
  6. customthe crude product was chromatographed on silica gel using
  7. additiona 9:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-47afcde8117e4480a78062719f2ed8c4
Source dataset
uspto-grants-2000_11
Patent number
US06150526

Reaction notes

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