3-Methoxypropylamine → HCID 57695546, compound

HRID 2079852Notes

Reaction equation

HRID 2079852 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([Br:26])=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:39][O:40][CH2:41][CH2:42][CH2:43][NH2:44]>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:15]([Br:26])=[CH:14][C:10]=1[C:11]([NH:44][CH2:43][CH2:42][CH2:41][O:40][CH3:39])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 16723-MethoxypropylamineHCID 682631,1'-CarbonyldiimidazoleHCID 469156382,4-Bis(benzyloxy)-5-bromobenzoic acid

Product 1

HCID 57695546HCID 57695546, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

2,4-Bis-benzyloxy-5-bromobenzoic acid (13.5 g, 33 mmol) was dissolved in DMF (anhydrous, 100 ml), and carbonyldiimidazole (CDI) (6.1 g, 37 mmol) was added and the resulting solution was stirred at r.t for 2 h. 3-Methoxypropylamine (3.6 g, 40 mmol) solution in DMF (25 ml) was added and the resulting solution was stirred at r.t. until the reaction was complete. The reaction was diluted with water (250 ml), extracted with ethyl acetate (250 ml×3), and the combined organics were washed thoroughly with water to remove DMF and dried over sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel to give 2,4-bis-benzyloxy-5-bromo-N-(3-methoxy-propyl)-benzamide (15.8 g, 99%). M.p.: 104-106° C.; 400 MHz 1H NMR (CDCl3) δ: 8.41 (s, 1H), 7.85 (t, J=5.2 Hz, 1H), 7.45-7.32 (m, 10H), 6.53 (s, 1H), 5.14 (s, 2H), 5.09 (s, 2H), 3.47-3.41 (q, J=5.2 Hz, 2H), 3.30 (t, J=6.4 Hz, 2H), 3.22 (s, 3H), 1.72-1.65 (pent, J=6.4 Hz, 2H); LCMS: 484, 486 [M+H].

Workup

  1. stirringthe resulting solution was stirred at r.t. until the reaction
  2. extractionextracted with ethyl acetate (250 ml×3)
  3. washthe combined organics were washed thoroughly with water
  4. customto remove DMF
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration and concentration
  7. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5679d9ae556f493d9e139330f0a158ab
Source dataset
uspto-grants-2011_04
Patent number
US07932279B2

Reaction notes

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