Hydrazine → 1-(3-aminopropyl)-N,N-diethyl-D-lysergamide

HRID 1016664Notes

Reaction equation

HRID 1016664 reaction equation
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][CH2:14][N:15]1[C:36]2[C:37]3[C:17]([CH2:18][C@@H:19]4[C:31]([C:32]=3[CH:33]=[CH:34][CH:35]=2)=[CH:30][C@@H:22]([C:23](=[O:29])[N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH2:21][N:20]4[CH3:38])=[CH:16]1.NN>CO>[NH2:3][CH2:12][CH2:13][CH2:14][N:15]1[C:36]2[C:37]3[C:17]([CH2:18][C@@H:19]4[C:31]([C:32]=3[CH:33]=[CH:34][CH:35]=2)=[CH:30][C@@H:22]([C:23](=[O:29])[N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])[CH2:21][N:20]4[CH3:38])=[CH:16]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 228945501-[3-(1,3-dihydro-1,3-dioxo-2 H-isoindol-2-yl)propyl]-N,N-diethyl-D-lysergamide

Product 1

HCID 228945531-(3-aminopropyl)-N,N-diethyl-D-lysergamideYield 79.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.1 g (4.1 mmol) of 9 in 35 mL of methanol was treated with 0.92 mL (29.3 mmol) of anhydrous hydrazine and stirred at room temperature overnight. The reaction was concentrated at reduced pressure. The residue was diluted with 25 mL of methylene chloride, undissolved solids were filtered off, and the filtrate was chromatographed on 300 g of silica gel using 15% methanol in methylene chloride as eluent to remove front running impurities, then 2% triethylamine and 15% methanol in methylene chloride as eluent to elute the product to yield 1.24 g (79.5%) of 10 as a yellow amorphous solid.

Workup

  1. concentrationThe reaction was concentrated at reduced pressure
  2. additionThe residue was diluted with 25 mL of methylene chloride, undissolved solids
  3. filtrationwere filtered off
  4. customthe filtrate was chromatographed on 300 g of silica gel using 15% methanol in methylene chloride as eluent
  5. customto remove front
  6. wash2% triethylamine and 15% methanol in methylene chloride as eluent to elute the product

Sources & evidence

ORD record
ord-e6e18867a0cd43d4905dae3cee6e88ca
Source dataset
uspto-grants-2002_11
Patent number
US06476199B1

Reaction notes

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