Ammonia → HCID 131725986, compound

HRID 1243743Notes

Reaction equation

HRID 1243743 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17]Cl)[C:12]=2[CH2:19][CH2:20][CH3:21])[CH:3]=1.[NH3:22].[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27]>CO>[C:23]([OH:30])(=[O:29])/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27].[NH2:22][CH2:17][C:13]1[C:12]([CH2:19][CH2:20][CH3:21])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[NH2:22][CH2:17][C:13]1[C:12]([CH2:19][CH2:20][CH3:21])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:4]1[CH:3]=[C:2]([Cl:1])[CH:9]=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 444972Fumaric AcidHCID 21930337HCID 21930337, compound

Product 1

HCID 131725986HCID 131725986, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-2-(3-chloromethyl-2-propylphenoxy)-benzonitrile (0.16 g, 0.50 mmol) in ammonia (7N in methanol, 25 mL, 175 mmol) was stirred for 65 h at ambient temperature. The solvent was removed in vacuo. The residue was treated with 10% sodium carbonate solution and extracted with ethyl acetate. The ethyl acetate layer was separated and a solution of fumaric acid (58 mg, 0.50 mmol) in methanol (3 mL) was added. After the solvent was removed in vacuo, the residue was triturated with diethyl ether overnight, collected by filtration, and dried to give 2-(3-aminomethyl-2-propyl-phenoxy)-4-chloro-benzonitrile hemifumarate (200 mg, 96%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. additionThe residue was treated with 10% sodium carbonate solution
  3. extractionextracted with ethyl acetate
  4. customThe ethyl acetate layer was separated
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was triturated with diethyl ether overnight
  7. filtrationcollected by filtration
  8. customdried

Sources & evidence

ORD record
ord-62c1408b5c9e4846858d130cb868d504
Source dataset
uspto-grants-2006_10
Patent number
US07119122B2

Reaction notes

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