3-Bromopropylamine hydrobromide → 2-(3-acetyl-phenoxy)-N-(3-bromopropyl)-acetamide

HRID 1182127Notes

Reaction equation

HRID 1182127 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([OH:11])=O)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.CN(C(=[N+](C)C)ON1C2=NC=CC=C2N=N1)C.Br.[Br:49][CH2:50][CH2:51][CH2:52][NH2:53]>CN(C=O)C>[C:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[O:7][CH2:8][C:9]([NH:53][CH2:52][CH2:51][CH2:50][Br:49])=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 787013-Bromopropylamine hydrobromideHCID 81531DiisopropylethylamineHCID 241887(3-Acetylphenoxy)acetic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 694112822-(3-acetyl-phenoxy)-N-(3-bromopropyl)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (3-acetyl-phenoxy)-acetic acid (0.194 g, 1.0 mmol) and diisopropylethylamine (0.38 g, 3 mmol) in dry DMF (3 ml) is treated with [dimethylamino-([1,2,3]triazolo[4,5-b]pyridin-3-yloxy)-methylene]-dimethyl-ammonium hexafluoro phosphate (0.38 g, 1.0 mmol). After stirring for 5 minutes 3-bromo-propylamine hydrobromide (0.26 g, 1.2 mmol) is added and stirring continued for a further 40 minutes. The solvent is evaporated and the crude mixture partitioned between ethylacetate and saturated aqueous NaHCO3. The ethyl acetate phase is dried over MgSO4 and evaporated to afford 2-(3-acetyl-phenoxy)-N-(3-bromopropyl)-acetamide. This crude material is taken up in acetonitrile (3 ml) and treated with triethylamine (0.38 g, 3 mmol) and 3-(4-fluoro-phenoxy)-azetidine hydrochloride (0.11 g, 1.2 mmol). The reaction mixture is stirred at ambient temperature for 20 hours, the solvent evaporated and the crude product purified by flash silica chromatography (elution 10:90 methanol/dichloromethane) to afford 2-(3-acetyl-phenoxy)-N-{3-[3-(4-fluoro-phenoxy)-azetidin-1-yl]-propyl}-acetamide. [MH]+ 401.14.

Workup

  1. additionis added
  2. customThe solvent is evaporated
  3. customthe crude mixture partitioned between ethylacetate and saturated aqueous NaHCO3
  4. dry with materialThe ethyl acetate phase is dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-0b5e4bc9fe7d4a2ea93ced35da96cf7f
Source dataset
uspto-grants-2007_10
Patent number
US07288537B2

Reaction notes

Loading…