1-Methylpiperazine → 3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl 4-methylpiperazine-1-carboxylate

HRID 2167203Notes

Reaction equation

HRID 2167203 reaction equation
[CH2:1]([CH2:11]/[C:12](/[CH3:21])=[CH:13]/[CH2:14][CH2:15]/[C:16](/[CH3:20])=[CH:17]/[CH2:18][OH:19])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].[CH3:34][N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:34][N:35]1[CH2:40][CH2:39][N:38]([C:22]([O:19][CH2:18][CH:17]=[C:16]([CH3:20])[CH2:15][CH2:14][CH:13]=[C:12]([CH3:21])[CH2:11][CH2:1][CH:2]=[C:3]([CH3:4])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])=[O:23])[CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 531671-MethylpiperazineHCID 682631,1'-CarbonyldiimidazoleHCID 5281365Geranylgeraniol

Product 1

HCID 781640563,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-yl 4-methylpiperazine-1-carboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 1 (160 mg, 55 mmol) in DCM (3 mL) at 0° C. was added carbonyldiimidazole (CDI) (107 mg, 0.66 mmol) and the reaction was stirred for 1 h. Then N-methylpiperazine (80 mg, 0.72 mmol) and DMAP (68 mg, 0.55 mmol) were added and stirred for 12 h. Solvent was removed and the residue was purified by column chromatography (DCM/MeOH) to give the carbamate 40a as a viscous oil in 88% yield (191 mg). TLC Rf: 0.54 (10% MeOH/DCM); 1H NMR (300 MHz, CDCl3): δ 5.34 (t, 3H), 5.08 (m, 3H), 4.59 (d, 2H), 3.49 (m, 4H), 2.35 (m, 4H), 2.29 (s, 3H), 2.10-1.97 (m, 12H), 1.70 (s, 3H), 1.67 (s, 3H), 1.59 (s, 9H); LCMS: MS (m/z): 417 (M+H).

Workup

  1. stirringstirred for 12 h
  2. customSolvent was removed
  3. customthe residue was purified by column chromatography (DCM/MeOH)

Sources & evidence

ORD record
ord-1050e955b60e4cccaf3b383301c65a72
Source dataset
uspto-grants-2015_06
Patent number
US09045403B2

Reaction notes

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