Hydrochloric Acid → 1,3,4,5-tetrahydro-1-{1-[(4-methyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)-methyl]-4-piperidinyl}-2H-imidazol-2-one

HRID 845382Notes

Reaction equation

HRID 845382 reaction equation
[CH:1]([C:3]1([CH3:17])[O:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[CH:15][CH:16]=[C:4]12)=O.Cl.[NH:19]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:29][CH2:28][NH:27][C:26]2=[O:30])[CH2:21][CH2:20]1.C([BH3-])#N.[Na+]>CO>[CH3:17][C:3]1([CH2:1][N:19]2[CH2:20][CH2:21][CH:22]([N:25]3[CH2:29][CH2:28][NH:27][C:26]3=[O:30])[CH2:23][CH2:24]2)[O:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]2[CH:14]=[CH:15][CH:16]=[C:4]12

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 5003444Sodium cyanoborohydrideHCID 130317571-(Piperidin-4-yl)imidazolidin-2-oneHCID 141830784-formyl-4-methyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine

Product 1

HCID 141830791,3,4,5-tetrahydro-1-{1-[(4-methyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)-methyl]-4-piperidinyl}-2H-imidazol-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.5 g of 4-formyl-4-methyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine in 50 ml of methanol is added 3.6 ml of 5.5N methanolic HCl and 3.4 g of 1,3,4,5-tetrahydro-1-(4-piperidinyl)-2H-imidazol-2-one followed by 900 mg of sodium cyanoborohydride. The reaction mixture is allowed to stir at room temperature for 8 days. 2 ml of conc. HCl is added to the reaction mixture and the solvent is removed by evaporation under reduced pressure. The residue is dissolved in 150 ml water and washed with 150 ml of 1:1 ethyl acetate-ether mixture. The aqueous phase is separated, basified with dilute sodium hydroxide to pH 9 and extracted with 2×150 ml of ethyl acetate. The combined ethyl acetate extracts are dried over anhydrous MgSO4, filtered, and the solvent is removed by evaporation under reduced pressure to yield 1,3,4,5-tetrahydro-1-{1-[(4-methyl-4H,6H-pyrrolo[ 1,2-a][4,1]benzoxazepin-4-yl)-methyl]-4-piperidinyl}-2H-imidazol-2-one which is characterized as its maleate salt, m.p. 197°-199°.

Workup

  1. customthe solvent is removed by evaporation under reduced pressure
  2. dissolutionThe residue is dissolved in 150 ml water
  3. washwashed with 150 ml of 1:1 ethyl acetate-ether mixture
  4. customThe aqueous phase is separated
  5. extractionextracted with 2×150 ml of ethyl acetate
  6. dry with materialThe combined ethyl acetate extracts are dried over anhydrous MgSO4
  7. filtrationfiltered
  8. customthe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-75414067f18d4915a0a190e7ac66f456
Source dataset
uspto-grants-1988_07
Patent number
US04758559

Reaction notes

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