Ammonium Hydroxide → HCID 178456164, compound

HRID 1199667Notes

Reaction equation

HRID 1199667 reaction equation
[CH:1]([N:4]1[C:18]2[C:19]3[C:6]([CH2:7][C@@H:8]4[C@@H:13]([C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:12][C@@H:11]([C:20]([OH:22])=O)[CH2:10][N:9]4[CH3:23])=[CH:5]1)([CH3:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.Cl.[NH2:38][CH2:39][CH2:40][C:41]1[N:45]=[CH:44][NH:43][CH:42]=1.[OH-].[NH4+]>CN(C)C=O.C(N(CC)CC)C>[NH:43]1[CH:42]=[C:41]([CH2:40][CH2:39][NH:38][C:20]([C@@H:11]2[CH2:12][C@H:13]3[C@@H:8]([CH2:7][C:6]4[C:19]5[C:18](=[CH:17][CH:16]=[CH:15][C:14]3=5)[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=4)[N:9]([CH3:23])[CH2:10]2)=[O:22])[N:45]=[CH:44]1

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 1825776-Methyl-1-(propan-2-yl)ergoline-8-carboxylic acidHCID 178478691HCID 178478691, compound

Product 1

HCID 178456164HCID 178456164, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a mixture of 3.5 g of (8β)-1-isopropyl-6-methylergoline-8-carboxylic acid in 80 ml of dimethylformamide were added 2.27 g of 1,1'-carbonyldiimidazole. After stirring for 3 hours at room temperature, the mixture was added dropwise to a solution of 2.27 g of histamine dihydrochloride in 100 ml of dimethylformamide to which 3.6 ml of triethylamine had been added. The reaction mixture was stirred at room temperature overnight and then poured into 2 liters of ice water to which 5 ml of ammonium hydroxide had been added. The resulting precipitate was recovered by filtration. The solid material was crystallized from methanol/water to provide 2.41 g of the desired title product hemihydrate as a light pink powder, m.p. 83°-86° C.

Workup

  1. additionhad been added
  2. stirringThe reaction mixture was stirred at room temperature overnight
  3. additionhad been added
  4. filtrationThe resulting precipitate was recovered by filtration
  5. customThe solid material was crystallized from methanol/water

Sources & evidence

ORD record
ord-2ec453b8ddc343e394623130d757e506
Source dataset
uspto-grants-1990_02
Patent number
US04902691

Reaction notes

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