1,2-Dichloroethane → 3-Benzyl-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine

HRID 857030Notes

Reaction equation

HRID 857030 reaction equation
[CH:1]12[CH2:11][CH:4]([C:5]3[C:10]1=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:3](O)[CH:2]2O.ClCCCl.I([O-])(=O)(=O)=O.[Na+].[CH2:24]([NH2:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH2:24]([N:31]1[CH2:2][CH:1]2[CH2:11][CH:4]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=32)[CH2:3]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7504BenzylamineHCID 131669751,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-diolHCID 23667635Sodium periodate

Product 1

HCID 120472193-Benzyl-2,3,4,5-tetrahydro-1H-1,5-methano-3-benzazepine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

1,2,3,4-Tetrahydro-1,4-methano-naphthalene-2,3-diol (40 g, 227.3 mmol) was stirred in H2O (1050 mL) and 1,2-dichloroethane (DCE) (420 mL) in a 2 L round bottom flask under nitrogen with cool water bath (10° C.). To this sodium periodate (NalO4) (51 g, 239 mmol) and triethylbenzyl ammonium chloride (Et3BnNCl) (50 mg) were added. The resulting mixture was stirred for 1 hour (slight initial exotherm), then the layers were separated and the aqueous layer was extracted with DCE (200 mL). The organic layer was washed with H2O (4×200 mL, or until no reaction to starch iodide is observed in the aqueous wash) then dried through a cotton plug. To this was added benzyl amine (25.5 g, 238.6 mmol) and the mixture was stirred for 2 minutes then immediately transferred into the sodium triacetoxyborohydride NaHB(OAc)3/DCE (see below) over 10 minutes.

Workup

  1. custom(10° C.)
  2. customwere separated
  3. extractionthe aqueous layer was extracted with DCE (200 mL)
  4. washThe organic layer was washed with H2O (4×200 mL
  5. customuntil no reaction to starch iodide
  6. washaqueous wash)
  7. customthen dried through a cotton plug
  8. stirringthe mixture was stirred for 2 minutes

Sources & evidence

ORD record
ord-a2734c58c5a44bb787745ebc6072eb91
Source dataset
uspto-grants-2006_12
Patent number
US07144882B2

Reaction notes

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