Sodium Cyanide → HCID 13019462, compound

HRID 2285733Notes

Reaction equation

HRID 2285733 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:18]2[NH:19][CH:20]=[CH:21][N:22]=2)[CH2:13][CH2:14][N:15]([CH3:17])[CH3:16])=[CH:8][CH:7]=1.[C-:23]#[N:24].[Na+]>O.Cl>[CH3:16][N:15]([CH2:14][CH2:13][CH:12]([C:9]1[CH:10]=[CH:11][C:6]([C:23]#[N:24])=[CH:7][CH:8]=1)[C:18]1[NH:19][CH:20]=[CH:21][N:22]=1)[CH3:17]

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 13019470HCID 13019470, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13019462HCID 13019462, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (0.3 g) in water (5 ml) was added dropwise to a stirred solution of 3-(4-aminophenyl)-N,N-dimethyl-3-(imidazol-2-yl) propanamine (1.0 g) in 2 N hydrochloric acid (6 ml) and water (6 ml), keeping the temperature at 3°-5°. After stirring for 30 min. the dark red solution was adjusted to pH 7-8 and treated with sodium cyanide (0.2 g) and cuprous cyanide (0.4 g) and heated on a steam bath for 3 h. The mixture was then adjusted to pH 11-12 and extracted with ethyl acetate (3×30 ml). The extracts were dried (Na2SO4) and concentrated to give the title compound as a gum (0.33 g) which was taken up into methanol (5 ml) and treated with a solution of maleic acid (0.15 g) in methanol (5 ml). Removal of the solvent and trituration of the residue with ether gave the dimaleate salt of the title compound as an off white solid that crystallised from ethanol-ether with m.p. 147°-148°; τ(D2O)2.06 to 2.35 (2H,m,aromatic),2.48(2H,br.s,imidazole), ##STR36## 6.5-7.5(4H,m,CH2CH2N(CH3)2),7.03(6H,s,N(CH3)2).

Workup

  1. customat 3°-5°
  2. temperatureheated on a steam bath for 3 h
  3. extractionextracted with ethyl acetate (3×30 ml)
  4. dry with materialThe extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-77d16dff2f4146b3a24847e4e314b0f5
Source dataset
uspto-grants-1982_04
Patent number
US04324792

Reaction notes

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