Sodium Carbonate → N,N-dimethyl-N'-[2-hydroxy-3-(1-piperidinyl)-propoxy]-N''-phenyl-guanidine hydrochloride

HRID 19752Notes

Reaction equation

HRID 19752 reaction equation
[NH2:1][O:2][CH2:3][CH:4]([OH:12])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.C([O-])([O-])=O.[Na+].[Na+].[CH3:19][N:20]([CH3:30])[C:21]([Cl:29])=[N:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)Cl>[ClH:29].[CH3:19][N:20]([CH3:30])[C:21]([NH:1][O:2][CH2:3][CH:4]([OH:12])[CH2:5][N:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)=[N:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 7131738[Chloro(phenylimino)methyl]dimethylamineHCID 187662101-(Aminooxy)-3-(piperidin-1-yl)propan-2-ol

Product 1

HCID 18766180N,N-dimethyl-N'-[2-hydroxy-3-(1-piperidinyl)-propoxy]-N''-phenyl-guanidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1150 mg (6.58 mmole) of 1-aminooxy-2-hydroxy-3-(1-piperidinyl)-propane (Ger. Off. 2 651 083) was dissolved in chloroform and 750 mg of Na2CO3 was added, then a solution of 1206 mg (6.58 mmole) of N,N-dimethyl-N′-phenyl-chloroformamidine (BR 888646/1959, Bayer, auth.: Kühle and Eue L.; CA 57, 136961/1962/) in 10 ml of chloroform was added dropwise. After 5 hours the solid state was filtered and the filtrate was evaporated. This residue (1800 mg oil) was dissolved in 10 ml of ethyl acetate, and the product was precipitated by addition of 10.46 ml of 0.54 N HCl/ethyl acetate. The yellow precipitate was filtered off, washed, and finally recrystallized from acetone, after ethyl acetate.

Workup

  1. filtrationAfter 5 hours the solid state was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThis residue (1800 mg oil) was dissolved in 10 ml of ethyl acetate
  4. customthe product was precipitated by addition of 10.46 ml of 0.54 N HCl/ethyl acetate
  5. filtrationThe yellow precipitate was filtered off
  6. washwashed
  7. customfinally recrystallized from acetone

Sources & evidence

ORD record
ord-4b1374f8828f48d5aae7a596dc1f46b3
Source dataset
uspto-grants-2010_06
Patent number
US07745465B2

Reaction notes

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