Triethylamine → 1,1-Dimethylethyl 7-iodo-1,3,4,5-tetrahydro-2h-2-benzazepine-2-carboxylate

HRID 1514178Notes

Reaction equation

HRID 1514178 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][NH:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:12]=1.[O:13](C(OC(C)(C)C)=O)[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=O.C(N(CC)CC)C>C(Cl)Cl>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:13])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 594035067-iodo-2,3,4,5-tetrahydro-1H-2-benzazepine

Product 1

HCID 594035231,1-Dimethylethyl 7-iodo-1,3,4,5-tetrahydro-2h-2-benzazepine-2-carboxylateYield 105.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-Iodo-2,3,4,5-tetrahydro-1H-2-benzazepine (Preparation 2) (450 mg, 1.648 mmol) was dissolved in DCM (30 ml) and treated with BOC2O (0.459 ml, 1.977 mmol) followed by triethylamine (0.459 ml, 3.30 mmol). The reaction mixture was stirred at RT for 30 minutes. LC/MS showed one major product. The reaction was washed with 0.5M HCl (20 ml), sat NaHCO3 (20 ml), dried over anhydrous MgSO4 and evaporated to yield the title compound (650 mg) as a colourless oil. MS (ES) C15H20INO2 requires 373; found 318 (M+H−56)+.

Workup

  1. washThe reaction was washed with 0.5M HCl (20 ml)
  2. dry with materialdried over anhydrous MgSO4
  3. customevaporated

Sources & evidence

ORD record
ord-9d7d6d8e6e214d0c83ca3fc8a3c4e519
Source dataset
uspto-grants-2012_07
Patent number
US08222245B2

Reaction notes

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