Formaldehyde → 3-Methyl-7-(4-fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine

HRID 1784423Notes

Reaction equation

HRID 1784423 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:21]=[C:20]([I:22])[C:14]3[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:13]=3[CH:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.O>ClCCl>[CH3:23][N:17]1[CH2:16][CH2:15][C:14]2[C:20]([I:22])=[CH:21][C:11]([S:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)(=[O:9])=[O:10])=[CH:12][C:13]=2[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 688303227-(4-Fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine

Product 1

HCID 688312513-Methyl-7-(4-fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepineYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-(4-fluorophenylsulfonyl)-9-iodo-1,2,4,5-tetrahydro-3-benzazepine (2.4 g, 5.5 mmol) in dichloromethane (20 ml) were added sodium triacetoxyborohydride (1.8 g, 8.5 mmol) and formalin (1 ml, 37%, 12 mmol). The mixture was stirred for 2 h without cooling then poured into water (100 ml) and extracted with more dichloromethane (100 ml). The resulting organic layer was washed with brine (100 ml), dried (MgSO4), and evaporated to give the subtitle compound as a white foam (2.4 g).

Workup

  1. temperaturewithout cooling
  2. extractionextracted with more dichloromethane (100 ml)
  3. washThe resulting organic layer was washed with brine (100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-45fb89563ed648a7b54d0cd553d9bb33
Source dataset
uspto-grants-2009_03
Patent number
US07504392B2

Reaction notes

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