N,N-Dimethyl-1,3-propanediamine → [10-(3-Dimethylaminopropylcarbamoyl)decyl]carbamic acid tert-butyl ester

HRID 2420742Notes

Reaction equation

HRID 2420742 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([OH:33])=O)=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH3:34][N:35]([CH3:40])[CH2:36][CH2:37][CH2:38][NH2:39]>O1CCCC1.ClCCl>[C:13]([O:17][C:18](=[O:19])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:33])[NH:39][CH2:38][CH2:37][CH2:36][N:35]([CH3:40])[CH3:34])([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 422929011-((tert-Butoxycarbonyl)amino)undecanoic acid

Product 1

HCID 86634233[10-(3-Dimethylaminopropylcarbamoyl)decyl]carbamic acid tert-butyl esterYield 61%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (118 mg, 0.73 mmol) was added to a solution of acid 3 (200 mg, 0.66 mmol) in a mixture of tetrahydrofuran (5 mL) and dichloromethane (1 mL). The resulting solution was stirred at ambient temperature for 4 h. 3-(Dimethylamino)propylamine (0.10 mL, 0.79 mmol) was then added and stirring continued for 14 hours at room temperature. The solvent was then removed under vacuum. The resulting residue was dissolved in dichloromethane (10 mL) and washed sequentially with aqueous sodium bicarbonate (1×10 mL), and then water (1×10 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated to give compound 4 (154 mg, 61%) as a clear oil: 1H NMR (500 MHz, CDCl3) δ 1.27 (m, 12H), 1.57 (br, 14H), 1.56-1.65 (m, 2H), 1.67-1.74 (m, 2H), 2.16 (t, 2H, J=7.5 Hz), 2.32 (s, 6H), 2.51 (t, 2H, J=6.7 Hz) 3.29-3.33 (m, 2H), 4.51 (br, 1H); m/z (ESI) 386 [C21H43N3O3+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for 14 hours at room temperature
  3. customThe solvent was then removed under vacuum
  4. dissolutionThe resulting residue was dissolved in dichloromethane (10 mL)
  5. washwashed sequentially with aqueous sodium bicarbonate (1×10 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e23997020b4948918b0204dec2b3d2ec
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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