Ammonia → 3-(12-Amino-2,3-dihydro-6-methyl-8alpha-ergolinyl)-1,1-diethylurea

HRID 35216Notes

Reaction equation

HRID 35216 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[C:8]([N+:18]([O-])=O)=[CH:9][CH:10]=[C:11]4[C:17]=3[C@H:14]([CH2:15]2)[CH2:13][NH:12]4)[CH2:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3]1.[BH4-].[Na+].Cl.N>CO.[Ni](Cl)Cl>[NH2:18][C:8]1[C:7]2=[C:17]3[C:11]([NH:12][CH2:13][CH:14]3[CH2:15][C@@H:16]3[C@@H:6]2[CH2:5][C@H:4]([NH:21][C:22](=[O:28])[N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])[CH2:3][N:2]3[CH3:1])=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 867423543-(2,3beta-Dihydro-6-methyl-12-nitro-8alpha-ergolinyl)-1,1-diethylurea

Product 1

HCID 867423533-(12-Amino-2,3-dihydro-6-methyl-8alpha-ergolinyl)-1,1-diethylureaYield 97.9%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 887MethanolSolvent

Procedure

One millimole of 3-(2,3β-dihydro-6-methyl-12-nitro-8α-ergolinyl)-1,1-diethylurea is dissolved in 25 ml of methanol, cooled in an ice bath, and 2 mmol of nickel chloride (with 6H2O) and thereafter 5 mmol of sodium borohydride are added thereto in 4-5 portions. Under ice cooling, the mixture is acidified with 2N hydrochloric acid, combined with dilute ammonia solution, and extracted by shaking. After drying and evaporation of the organic phase, 350 mg of 3-(12-amino-2,3-dihydro-6-methyl-8α-ergolinyl)-1,1-diethylurea is obtained. [α]D =-31° (0.5% methanol) as the tartaric acid salt (1:1).

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted
  3. customAfter drying
  4. customevaporation of the organic phase

Sources & evidence

ORD record
ord-b169d22a5d9144fe95757e94cc83b450
Source dataset
uspto-grants-1988_08
Patent number
US04766128

Reaction notes

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