Ammonium Hydroxide → HCID 22273744, compound

HRID 1064380Notes

Reaction equation

HRID 1064380 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[C:12]2[CH2:13][CH2:14][CH:15]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)=[O:20])[CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1.[NH4+].[OH-]>C(Cl)Cl>[OH:6][C:7]1[C:12]2[CH2:13][CH2:14][CH:15]([C:19]([N:21]3[CH2:26][CH2:25][CH:24]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:23][CH2:22]3)=[O:20])[CH2:16][C:17](=[O:18])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 25134Boron tribromideHCID 21936980HCID 21936980, compound

Product 1

HCID 22273744HCID 22273744, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under a nitrogen atmosphere, 2.2 mL (0.0234 mol) of BBr3 were added to 20 mL of CH2Cl2, then 1.47 g (0.0039 mol) of (±)-1-methoxy-7-[(4-phenylpiperidin-1-yl)carbonyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one dissolved in 25 mL of CH2Cl2 were added dropwise at room temperature. The reaction mixture was stirred for 2 h, then it was poured onto 25 g of crushed ice, basified with conc. NH4OH and extracted with CH2Cl2. The organic layer was dried and the solvent was removed in vacuo. The resulting crude solid was triturated with Et2O, filtered and dried, yielding 1.16 g of the title product.

Workup

  1. additionwere added dropwise at room temperature
  2. extractionextracted with CH2Cl2
  3. customThe organic layer was dried
  4. customthe solvent was removed in vacuo
  5. customThe resulting crude solid was triturated with Et2O
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-b7e1fe1862cb4d0a85d142913308e0da
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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