Dibenzylamine → HCID 12952415, compound

HRID 1390917Notes

Reaction equation

HRID 1390917 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br[CH2:18][C:19]([C:21]1[CH:22]=[CH:23][C:24]([N:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[C:25]([S:27]([NH2:30])(=[O:29])=[O:28])[CH:26]=1)=[O:20]>CC(=O)CC>[OH:20][CH:19]([C:21]1[CH:22]=[CH:23][C:24]([N:31]2[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]2)=[C:25]([S:27]([NH2:30])(=[O:28])=[O:29])[CH:26]=1)[CH2:18][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 12952395HCID 12952395, compound

Product 1

HCID 12952415HCID 12952415, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

A solution of dibenzylamine (3.34 g) in butanone (10 ml) was added to a vigorously sitrred suspension of 5-(2-bromoacetyl)-2-(1-piperidinyl)benzenesulphonamide, hydrobromide (2.5 g) in butanone (100 ml). After 3 hours the mixture was filtered and the filtrate concentrated to a yellow oil. This oil was dissolved in ethanol (100 ml) and treated with sodium broohydride (0.42 g) at room temperature. After 1 hour, excess borohydride was destroyed with 2N hydrochloric acid. Ethanol was removed, the residue basified with 8% sodium bicarbonate solution and extracted with ethyl acetate (3 × 100 ml). The extracts were washed with water (100 ml), dried, and concentrated to a pale yellow oil (2.7 g). This was chromatographed on Merck Kieselgel 60 (50 g) to give the product as a white solid, 2 g, m.p. 133°-142°.

Workup

  1. filtrationAfter 3 hours the mixture was filtered
  2. concentrationthe filtrate concentrated to a yellow oil
  3. dissolutionThis oil was dissolved in ethanol (100 ml)
  4. additiontreated with sodium broohydride (0.42 g) at room temperature
  5. customexcess borohydride was destroyed with 2N hydrochloric acid
  6. customEthanol was removed
  7. extractionextracted with ethyl acetate (3 × 100 ml)
  8. washThe extracts were washed with water (100 ml)
  9. customdried
  10. concentrationconcentrated to a pale yellow oil (2.7 g)
  11. customThis was chromatographed on Merck Kieselgel 60 (50 g)

Sources & evidence

ORD record
ord-a9c716205fb842c08d154846be5e6f16
Source dataset
uspto-grants-1979_02
Patent number
US04140713

Reaction notes

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