Carbon tetrabromide → HCID 86646584, compound

HRID 2080555Notes

Reaction equation

HRID 2080555 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH:14](O)[CH3:15])[CH2:10][CH2:11][O:12][CH3:13])=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:18].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:18][CH2:15][CH2:14][N:9]([CH2:8][C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:10][CH2:11][O:12][CH3:13]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 86646585HCID 86646585, compound

Product 1

HCID 86646584HCID 86646584, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.) solution of 1.25 grams (0.0051 mole) of 2-{[(6-chloro(3-pyridyl)methyl](2-methoxyethyl)amino}ethan-1-ol and 1.9 grams (0.0057 mole) of carbon tetrabromide in 70 mL of methylene chloride was added 1.66 grams (0.0064 mole) of triphenylphosphine. The reaction mixture was allowed to warm to ambient temperature where it stirred for 1.5 hours. After this time silica gel was added and the mixture concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel eluting with a 50/50 mixture of diethyl ether and hexanes. The appropriate fractions were combined and concentrated under reduced pressure, yielding 1.17 grams of (2-bromoethyl)[(6-chloro(3-pyridyl))methyl](2-methoxyethyl)amine as an oil. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionAfter this time silica gel was added
  2. concentrationthe mixture concentrated under reduced pressure to a residue
  3. additionThe residue was subjected to column chromatography on silica gel eluting with a 50/50 mixture of diethyl ether and hexanes
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eee084bf6098498984da72bc702834de
Source dataset
uspto-grants-2011_04
Patent number
US07932393B2

Reaction notes

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