Formaldehyde → HCID 21481152, compound

HRID 435706Notes

Reaction equation

HRID 435706 reaction equation
N[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1.C=O.[C:33](#N)C.[C:36]([BH3-])#[N:37].[Na+]>C(O)(=O)C>[CH3:33][N:37]([CH3:36])[C:2]1[CH:30]=[CH:29][C:5]2[S:6][C:7]3[CH:28]=[CH:27][CH:26]=[CH:25][C:8]=3[CH:9]([N:11]3[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][N:19]4[CH2:23][CH2:22][O:21][C:20]4=[O:24])[CH2:13][CH2:12]3)[CH2:10][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 6342AcetonitrileHCID 5003444Sodium cyanoborohydrideHCID 21481150HCID 21481150, compound

Product 1

HCID 21481152HCID 21481152, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

7 g of 3-[ 2-[4-(2-amino-10,11-dihydro-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl ]-2-oxazolidinone, 13.1 ml of 40% formaldehyde and 61 ml of acetonitrile are treated with 3.32 g of sodium cyanoborohydride and the resulting mixture is treated dropwise over a period of 10 minutes with 1.5 ml of acetic acid. The mixture is stirred for a further 90 minutes, treated dropwise with a further 1.5 ml of acetic acid and again stirred for 15 minutes. The mixture is now extracted with 200 ml of ether and the organic phase washed three times with 1-N aqueous potassium hydroxide solution, dried over sodium sulphate and evaporated. There is obtained 3-[ 2-[4-(10,11-dihydro-2-dimethylamino-dibenzo[b,f]thiepin-10-yl)-1-piperazinyl]-ethyl ]-2-oxazolidinone which melts at 168°-170° C. After recrystallisation from ethanol, this compound melts at 171°-173° C. By treatment with maleic acid there is obtained the corresponding maleate which melts at 143.5°-144.5° C after recrystallisation from acetonitrile.

Workup

  1. stirringagain stirred for 15 minutes
  2. extractionThe mixture is now extracted with 200 ml of ether
  3. washthe organic phase washed three times with 1-N aqueous potassium hydroxide solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-6534d28ba0e24c3ca39bf7318beca5c3
Source dataset
uspto-grants-1977_02
Patent number
US04006144

Reaction notes

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