1,4-Dioxane hydrochloride → HCID 178462018, compound

HRID 1691695Notes

Reaction equation

HRID 1691695 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]([CH2:26][N:27]([C@@H:35]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[CH3:36])C(=O)OC(C)(C)C)[CH2:15]1.[ClH:47].O1CCOCC1>O1CCOCC1>[ClH:47].[F:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:12][N:11]=[N:10][N:9]=2)[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[CH2:19][CH2:18][CH:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:16]([CH2:26][NH:27][C@@H:35]([C:37]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH:40]=[CH:39][CH:38]=2)[CH3:36])[CH2:15]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 178461651HCID 178461651, compound

Product 1

HCID 178462018HCID 178462018, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 206 mg of the crude product of tert-butyl ({1-[2,6-difluoro-4-(1H-tetrazol-5-yl)phenyl]-4-phenylpiperidin-3-yl}methyl)[(1R)-1-(1-naphthyl)ethyl]carbamate were added 2.0 mL of 1,4-dioxane and 2.0 mL of a 4 M hydrogen chloride/1,4-dioxane solution, followed by stirring at room temperature for 2 days. The reaction mixture was concentrated under reduced pressure, and to the residue were then added ethyl acetate and a small amount of ethanol, followed by heating for dissolution. Hexane was added thereto, and the precipitate was isolated by filtration, and dried under reduced pressure to obtain 153 mg of (1R)—N-({1-[2,6-difluoro-4-(1H-tetrazol-5-yl)phenyl]-4-phenylpiperidin-3-yl}methyl)-1-(1-naphthyl)ethaneamine hydrochloride as a beige solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperatureby heating for dissolution
  3. additionHexane was added
  4. customthe precipitate was isolated by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-5a7991b040434d7d9440e36f5497f5c8
Source dataset
uspto-grants-2012_04
Patent number
US08153658B2

Reaction notes

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