Dodecylamine → HCID 67187025, compound

HRID 735839Notes

Reaction equation

HRID 735839 reaction equation
[CH2:1]([NH2:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].CCN(C(C)C)C(C)C.[Cl:23][CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1>C(Cl)Cl>[Cl:23][CH2:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:30])=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 13583DodecylamineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 67187025HCID 67187025, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The resin-bound dodecylamine (described in step a, 0.0426 mmol) was swelled in DCM (1.0 mL) for 15 min at rt. DIEA (28 mg, 0.213 mmol) and 4-chloromethylbenzoyl chloride (40 mg, 0.213 mmol) were added and the reaction mixture was shaken at 0° C. for 2 h then 14 h at rt. The resin was washed successively with THF (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min). The resin was then dried under vacuum to afford the resin-bound 4-chloromethyl-N-dodecyl-benzamide which was used directly in the next step.

Workup

  1. custom14 h
  2. customat rt
  3. washThe resin was washed successively with THF (1×15 min), MeOH (1×15 min), THF (1×15 min), MeOH (3×10 min), DMF (3×10 min), MeOH (1×5 min), THF (3×10 min), MeOH (1×5 min), DCM (3×10 min) and with Et2O (1×10 min)
  4. customThe resin was then dried under vacuum

Sources & evidence

ORD record
ord-205069e9b96b4bd6ab6d9570ef3455e7
Source dataset
uspto-grants-2009_09
Patent number
US07592477B2

Reaction notes

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