Ammonium Chloride → HCID 12532948, compound

HRID 1182732Notes

Reaction equation

HRID 1182732 reaction equation
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].C([Mg]Cl)C.[Mg].[CH2:15]([N:22]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCCC.C(OCC)(=O)C.O>[CH2:15]([N:22]1[CH2:28][CH2:27][CH2:26][C:25]([C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH2:4][OH:5])([OH:29])[CH2:24][CH2:23]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 728502-Bromobenzyl alcoholHCID 15143501-Benzyl-hexahydro-4H-azepin-4-oneHCID 5462224MagnesiumHCID 178461633HCID 178461633, compound

Product 1

HCID 12532948HCID 12532948, compoundYield 61.2%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent2×HCID 8900HeptaneSolvent

Procedure

To a solution of 2-bromobenzyl alcohol (7.8 g, 42 mmol) in tetrahydrofuran (80 ml) was added dropwise a 2.8 M solution of ethylmagnesium chloride in tetrahydrofuran (15 ml, 42 mmol). The reaction was exothermic, and the rate of addition was adjusted to maintain a gentle reflux. After completed addition magnesium turnings (1.0 g, 42 mmol) were added in portions. The mixture was heated at reflux for 2 h before addition of a solution of 1-benzyl-azepan-4-one (8.5 g, 42 mmol) in tetrahydrofuran (40 ml). The reaction mixture was heated for another 4 h at reflux. Cooling to room temperature was followed by slow addition of saturated ammonium chloride solution (50 ml), water (100 ml) and ethyl acetate (300 ml). The layers were separated, and the organic layer was concentrated to give a green oil. Flash column chromatography using a 2:1 mixture of heptane and ethyl acetate as eluent gave the title compound as a light yellow oil (8.0 g, 61%).

Workup

  1. additionthe rate of addition
  2. temperatureto maintain a gentle reflux
  3. additionwere added in portions
  4. temperatureThe mixture was heated
  5. temperatureThe reaction mixture was heated for another 4 h
  6. temperatureat reflux
  7. customThe layers were separated
  8. concentrationthe organic layer was concentrated
  9. customto give a green oil

Sources & evidence

ORD record
ord-8072daff056546fc8067d991124f3943
Source dataset
uspto-grants-2014_03
Patent number
US08664216B2

Reaction notes

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