Pyridine → HCID 57267718, compound

HRID 1351877Notes

Reaction equation

HRID 1351877 reaction equation
N[C:2]1[CH:31]=[CH:30][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([N:11]([CH2:19][C@H:20]([OH:29])[CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:10][C:4]=2[CH:3]=1.C(Cl)(=O)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.[N:41]1C=CC=CC=1.[C:47](=[O:50])([O-])O.[Na+]>CN(C)C1C=CN=CC=1.ClCCl>[CH2:12]([N:11]([C:9]1[C:8]([NH:41][C:47](=[O:50])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:7][C:6]2[CH2:5][CH2:4][CH2:3][CH2:2][CH2:31][C:30]=2[CH:10]=1)[CH2:19][C@H:20]([OH:29])[CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 57152468HCID 57152468, compound

Product 1

HCID 57267718HCID 57267718, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, a solution of (2S)-1-[N-(3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-N-benzylamino]-3-phenoxy-2-propanol (150 mg), benzoyl chloride (44 μl), pyridine (35 μl), and catalytic amounts of 4-dimethylaminopyridine in dichloromethane (5 ml) was stirred at room temperature for 5 hours. The resulting mixture was poured into saturated aqueous sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1) to give N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]-3-benzoylamino-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine (163 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-4bdbbf70f0fd41a384cf4b7b1ae71b0c
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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