Ammonium Chloride → HCID 19968909, compound

HRID 976152Notes

Reaction equation

HRID 976152 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.CCCCC.[CH2:28]([N:35]1[CH2:40][CH2:39][CH:38]([CH2:41][CH:42]=[O:43])[CH2:37][CH2:36]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][CH:42]([OH:43])[CH2:41][CH:38]2[CH2:37][CH2:36][N:35]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:40][CH2:39]2)=[CH:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 100136024-Piperidineacetaldehyde, 1-(phenylmethyl)-HCID 15373979tert-Butyl (4-acetylphenyl)carbamateHCID 178446069HCID 178446069, compound

Product 1

HCID 19968909HCID 19968909, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

50 ml of tetrahydrofuran was added to 3.80 g of N-t-butoxycarbonyl-4-acetylaniline, and 19.0 ml of a 1.7M t-butyl lithium·pentane solution was added dropwise thereto under an argon stream at -78° C. Subsequently, a solution of 3.50 g of (1-benzylpiperidin-4-yl)acetaldehyde dissolved in 10 ml of tetrahydrofuran was added to the mixture, and the resulting mixture was stirred until its temperature was returned to room temperature. Then, a saturated ammonium chloride aqueous solution was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was dried over anhydrous sodium sulfate. Then, the solvent was removed by distillation under reduced pressure, and the obtained residue was applied to silica gel column chromatography to obtain 4.57 g of the title compound as white powder.

Workup

  1. additionwas added dropwise
  2. customat -78° C
  3. additionwas added to the mixture
  4. customwas returned to room temperature
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialthe extract was dried over anhydrous sodium sulfate
  7. customThen, the solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-6db4b4f680504aa88003c129d4088ba5
Source dataset
uspto-grants-1997_03
Patent number
US05610303

Reaction notes

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