3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide → 3-chloro-N-(3-formyl-1-adamantyl)benzamide

HRID 1503261Notes

Reaction equation

HRID 1503261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][C:10]([CH2:18][OH:19])([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]12[CH2:15][CH:14]3[CH2:13][CH:12]([CH2:11][C:10]([CH:18]=[O:19])([CH2:16]3)[CH2:9]1)[CH2:17]2)=[O:6]

Participants

4

Reactant 2

HCID 1177026323-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamideHCID 178418287HCID 178418287, compound

Product 1

HCID 1177027713-chloro-N-(3-formyl-1-adamantyl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-chloro-N-[3-(hydroxymethyl)-1-adamantyl]benzamide (200 mg, 0.63 mmol) in DCM (15 mL) was added PCC (200 mg, 0.93 mmol) in one portion and the reaction mixture was stirred at room temperature for two hours. The reaction mixture was then filtered through a pad of silica gel and the filtrate was concentrated under reduced pressure to give 200 mg (100%) of crude title compound, 3-chloro-N-(3-formyl-1-adamantyl)benzamide, as a brown oil. ESI-MS m/z: 318 (M+H)+.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c6b2de9a5fbe410eab63bfc317f61f15
Source dataset
uspto-grants-2015_12
Patent number
US09212165B2

Reaction notes

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