Dichloromethane → 3-Benzylamino-4-[3-(3-piperidinomethylphenoxy)propylamino]-1,2,5-thiadiazole

HRID 280413Notes

Reaction equation

HRID 280413 reaction equation
Cl.Cl.Cl.[CH2:4]([NH:11][C:12](=[NH:33])[C:13](=[NH:32])[NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:20]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C(Cl)Cl.[S:37](N1C(=O)C2=CC=CC=C2C1=O)N1C(=O)C2=CC=CC=C2C1=O>C(N(CC)CC)C>[CH2:4]([NH:11][C:12]1[C:13]([NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH2:25][N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]3)[CH:20]=2)=[N:32][S:37][N:33]=1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 821962,2'-Thiobis(1H-isoindole-1,3(2H)-dione)HCID 178478597HCID 178478597, compound

Product 1

HCID 133136883-Benzylamino-4-[3-(3-piperidinomethylphenoxy)propylamino]-1,2,5-thiadiazoleYield 77.3%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of N-benzyl-N'-[3-(3-piperidinomethylphenoxy)propyl]ethanediimidamide trihydrochloride (4.73 g; 9.16 mmoles) [prepared in Step A], 45 ml of CH2Cl2 and 3.8 ml of triethylamine was treated with N,N'-thiobisphthalimide (DMF solvate) (3.64 g; 9.16 mmoles) and stirred for one hour. The mixture was washed with 44 ml of 10% KOH, dried (MgSO4), filtered, diluted with toluene and concentrated. The residue was chromatographed by flash chromatography on 110 g of silica gel (230-400 mesh) using ethyl acetate as the eluent to give 3.1 g (77%) of the title compound. Treatment of the product with an equivalent amount of aqueous HCl in 2-propanol gave the hydrochloride salt of the title compound, mp 138°-141° C.

Workup

  1. washThe mixture was washed with 44 ml of 10% KOH
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. additiondiluted with toluene
  5. concentrationconcentrated
  6. customThe residue was chromatographed by flash chromatography on 110 g of silica gel (230-400 mesh)

Sources & evidence

ORD record
ord-0ac5500afba94dd2bfc8277e80d6928c
Source dataset
uspto-grants-1986_05
Patent number
US04588826

Reaction notes

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