Phenethylamine → [1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl ester

HRID 337218Notes

Reaction equation

HRID 337218 reaction equation
S(Cl)(Cl)=O.[C:5]([O:9][C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([S:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[C:24]([F:31])[CH:23]=2)(=[O:21])=[O:20])[CH2:15][CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].N1C=CC=CC=1.[CH2:38]([NH2:46])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl>[C:5]([O:9][C:10](=[O:11])[NH:12][CH:13]1[CH2:14][CH2:15][N:16]([S:19]([C:22]2[CH:30]=[CH:29][C:25]([C:26](=[O:28])[NH:46][CH2:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[C:24]([F:31])[CH:23]=2)(=[O:20])=[O:21])[CH2:17][CH2:18]1)([CH3:7])([CH3:8])[CH3:6]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 710601234-(4-tert-Butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid

Product 1

HCID 71060106[1-(3-Fluoro-4-phenethylcarbamoyl-benzenesulfonyl)-piperidin-4-yl]-carbamic acid tert-butyl esterYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Thionyl chloride (0.16 g, 2.2 mmol) was added dropwise to a stirred solution of 4-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-2-fluoro-benzoic acid (0.3 g, 0.75 mmol) and pyridine (0.36 ml, 4.5 mmol) in DCM (10 ml). The reaction mixture was stirred at room temperature under a nitrogen atmosphere for 4 hours, after this time phenethylamine (0.19 ml, 1.5 mmol) was added in one portion and stirring was continued for a further 12 hours. The mixture was then diluted with DCM (10 ml) before being washed sequentially with HCl (1M solution, 10 ml) and NaOH (1M solution, 10 ml). The organic layer was separated, dried (MgSO4), filtered and concentrated to give the title compound (0.38 g, 74%) as a white foam which was taken on without further purification. Tr=2.16 min m/z (ES+) (M+Na+) 528.

Workup

  1. stirringstirring
  2. waitwas continued for a further 12 hours
  3. washbefore being washed sequentially with HCl (1M solution, 10 ml) and NaOH (1M solution, 10 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-23c5ce2b9fbe4768b6193d9812187517
Source dataset
uspto-grants-2014_11
Patent number
US08889716B2

Reaction notes

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