Nitrogen → 7-azido-N-(phenylmethyl)heptanamide

HRID 2375132Notes

Reaction equation

HRID 2375132 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=O)=[N+:2]=[N-:3].C1N=CN(C(N2C=NC=C2)=O)C=1.N#N.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:34][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:12])=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 947NitrogenHCID 7504BenzylamineHCID 682631,1'-CarbonyldiimidazoleHCID 22907807HCID 22907807, compound2×

Product 1

HCID 249950687-azido-N-(phenylmethyl)heptanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-azido-N-(phenylmethyl)heptanamide (65) was synthesized from 7-zidoheptanoic acid (64) as shown above. To 120 mg crude 7-azidoheptanoic acid (64) (0.7 mmol, 1.0 eq) was added 1 mL anhydrous THF. To the stirring solution was added 120 mg CDI (0.74 mmol, 1.06 eq) at room temperature. N2 was rapidly evolved from the yellowish slurry. The resulting transparent solution stirred at room temperature for 0.5 h. To the solution was then added 82.5 mg benzylamine (0.77 mmol, 1.1 eq). The solution was stirred 2 h at room temperature followed by solvent removal in vacuo and silica gel chromatography (2:2:1; petroleum ether:Et2O:EtOAc) to render 65 in as a waxy solid (108 mg, 60%). Lyophilization from 50% aqueous CH3CN afforded a fluffy white powder. m.p. slightly above ambient temperature.

Workup

  1. stirringThe solution was stirred 2 h at room temperature
  2. customfollowed by solvent removal in vacuo and silica gel chromatography (2:2:1; petroleum ether:Et2O:EtOAc)
  3. customLyophilization from 50% aqueous CH3CN afforded a fluffy white powder
  4. customm.p. slightly above ambient temperature

Sources & evidence

ORD record
ord-e30226b2ef5e44cc91a1451681f71bad
Source dataset
uspto-grants-2008_12
Patent number
US07465544B2

Reaction notes

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