Triethylamine → 1-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamide

HRID 1016663

Reaction equation

HRID 1016663 reaction equation
NC(C)[CH2:3][CH2:4][N:5]1[C:26]2[C:27]3[C:7]([CH2:8][C@@H:9]4[C:21]([C:22]=3[CH:23]=[CH:24][CH:25]=2)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]4[CH3:28])=[CH:6]1.[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32].[CH2:42]([N:44](CC)CC)[CH3:43]>C1COCC1>[N:30]([C:33]1[CH:41]=[CH:40][C:36]([C:37]([NH:44][CH2:42][CH2:43][CH2:3][CH2:4][N:5]2[C:26]3[C:27]4[C:7]([CH2:8][C@@H:9]5[C:21]([C:22]=4[CH:23]=[CH:24][CH:25]=3)=[CH:20][C@@H:12]([C:13](=[O:19])[N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH2:11][N:10]5[CH3:28])=[CH:6]2)=[O:38])=[CH:35][CH:34]=1)=[C:31]=[S:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6376544-Isothiocyanatobenzoyl chlorideHCID 228945521-(3-aminobutyl)-N,N-diethyl-D-lysergamide

Product 1

HCID 228945541-[[[(4-isothiocyanatophenyl)carbonyl]amino]butyl]-N,N-diethyl-D-lysergamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 370 mg (0.94 mmol) of 5 in 15 mL of dry THF was cooled to 0° C. and treated with a solution of 190 mg (0.96 mmol) of 6 in 5 mL of dry THF, stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was treated with 0.14 mL (1.0 mmol) of triethylamine and stirred at room temperature for 2 hours The reaction mixture was concentrated at reduced pressure. The residue was dissolved in methylene chloride, washed with H2O, dried over anhydrous sodium sulfate and concentrated at reduced pressure. The residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent to yield 325 mg (62%) of 7 as a tan amorphous solid [α]D=+47.5° (c=0.91%; CHCl3).

Workup

  1. customat room temperature
  2. customovernight
  3. stirringstirred at room temperature for 2 hours The reaction mixture
  4. concentrationwas concentrated at reduced pressure
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washwashed with H2O
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated at reduced pressure
  9. customThe residue was chromatographed on 200 g of silica gel using 3% methanol in methylene chloride as eluent

Sources & evidence

ORD record
ord-c7813d691e3849cc95036e9426a1ea7e
Source dataset
uspto-grants-2002_11
Patent number
US06476199B1

Linked notes

Loading…