Triethylamine → 3-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

HRID 1965958Notes

Reaction equation

HRID 1965958 reaction equation
CS([Cl:5])(=O)=O.[C:6]([O:10][C:11]([N:13]1[CH2:19][CH2:18][C:17]2[C:20]([CH2:25]O)=[C:21]([Cl:24])[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>C(Cl)Cl>[C:6]([O:10][C:11]([N:13]1[CH2:19][CH2:18][C:17]2[C:20]([CH2:25][Cl:5])=[C:21]([Cl:24])[CH:22]=[CH:23][C:16]=2[CH2:15][CH2:14]1)=[O:12])([CH3:9])([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 597873733-tert-butoxycarbonyl-7-chloro-6-hydroxymethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Product 1

HCID 597874103-tert-Butoxycarbonyl-7-chloro-6-chloromethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add methanesulfonyl chloride (1.1 g, 9.63 mmol; alternatively 2.36 g, 20.7 mmol) to 3-tert-butoxycarbonyl-7-chloro-6-hydroxymethyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine (2.5 g, 8.03 mmol; alternatively 3.2 g, 10.3 mmol) and triethylamine (2.2 mL, 16.06 mmol; alternatively 4.3 mL, 30.8 mmol) in DCM (50 mL; alternatively 60 mL) at 0° C. Warm the mixture to room temperature and stir for 1 h., alternatively for 16 h. Dilute the reaction with DCM and wash the organic phase with water. Dry the organic phase over Na2SO4, filter and concentrate in vacuo to afford the title compound as a clear oil that was used immediately without any further purification. MS (ES+) m/z: 274 [M-(t-Bu)+H]+.

Workup

  1. customat 0° C
  2. additionDilute
  3. washwash the organic phase with water
  4. dry with materialDry the organic phase over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-16bb912e6f244365b67a7675578ef2fc
Source dataset
uspto-grants-2013_04
Patent number
US08420631B2

Reaction notes

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