1-Bromo-3-chloropropane → HCID 86729497, compound

HRID 712484Notes

Reaction equation

HRID 712484 reaction equation
[CH3:1][N:2]([CH3:9])[CH:3]1[CH:8]2[CH:4]1[CH2:5][NH:6][CH2:7]2.Br[CH2:11][CH2:12][CH2:13][Cl:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[Cl:14][CH2:13][CH2:12][CH2:11][N:6]1[CH2:7][CH:8]2[CH:4]([CH:3]2[N:2]([CH3:9])[CH3:1])[CH2:5]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 10796Cesium carbonateHCID 55299712HCID 55299712, compound

Product 1

HCID 86729497HCID 86729497, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N,N-dimethyl-3-azabicyclo[3.1.0]hexan-6-amine (1.45 g), 1-bromo-3-chloropropane (4.05 mL) and cesium carbonate (11.20 g) in acetone was heated to reflux for 7 h, cooled to rt and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 35:1 (v/v) DCM/MeOH) to afford the title compound as yellow oil (0.93 g, 40.00%), HPLC: 80.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 203.7 (M+1).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 7 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 35:1 (v/v) DCM/MeOH)

Sources & evidence

ORD record
ord-c785724f79604c6999fc283589e299c3
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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