Cycloheptylamine → HCID 2843132, compound

HRID 1670518Notes

Reaction equation

HRID 1670518 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:18]1([NH2:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:25][CH:18]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2899CycloheptylamineHCID 8471TriethylamineHCID 685154-Bromobenzoyl chloride

Product 1

HCID 2843132HCID 2843132, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 4-bromo-benzoyl chloride (2.0 g, 9.1 mmol) in DCM (20 mL). Cool the solution to 0° C. and add triethylamine (2.54 mL, 18.2 mmol) followed by cycloheptylamine (1.24 g, 10.9 mmol). Warm the mixture to room temperature over 1 h. Wash the mixture with saturated NaHCO3 (15 mL). Collect the organic layer, and extract the aqueous layer with DCM. Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo. Purify the residue by chromatography on silica gel (120 g) eluting with hexane/EtOAc (1:1) to obtain the title compound as a solid (2.5 g, 93%). MS (APCI+) m/z: 296 (M)+.

Workup

  1. temperatureWarm the mixture to room temperature over 1 h
  2. washWash the mixture with saturated NaHCO3 (15 mL)
  3. customCollect the organic layer
  4. extractionextract the aqueous layer with DCM
  5. dry with materialDry the combined organic extracts over Na2SO4
  6. filtrationfilter
  7. concentrationconcentrate in vacuo
  8. customPurify the residue by chromatography on silica gel (120 g)
  9. washeluting with hexane/EtOAc (1:1)

Sources & evidence

ORD record
ord-a96ceded034a4664ae0fb63e901d4ed9
Source dataset
uspto-grants-2011_08
Patent number
US07994163B2

Reaction notes

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