Phenyltrimethylammonium bromide dibromide → HCID 86749704, compound

HRID 1077562Notes

Reaction equation

HRID 1077562 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:31]=[CH:30][C:28]([CH3:29])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[C:17]1[CH:16]=[N:15][C:14]([C:32](=[O:34])[CH3:33])=[C:13]([CH2:35][O:36][CH3:37])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:38].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[N:18]([S:22]([C:25]1[CH:26]=[CH:27][C:28]([CH3:29])=[CH:30][CH:31]=1)(=[O:24])=[O:23])[C:17]1[CH:16]=[N:15][C:14]([C:32](=[O:34])[CH2:33][Br:38])=[C:13]([CH2:35][O:36][CH3:37])[C:12]2=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 19431937HCID 19431937, compound

Product 1

HCID 86749704HCID 86749704, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.29 g of 6-benzyloxy-4-methoxymethyl-3-acetyl-9-tosyl-β-carboline is stirred with the double molar amount of phenyltrimethylammonium tribromide in 100 ml of absolute tetrahydrofuran for 4 days at room temperature. The reaction mixture is evaporated to dryness, taken up in methylene chloride, washed with saturated NaCl solution, dried on Sikkon and concentrated by evaporation. The crude product is chromatographed on silica gel (cyclohexane/ethyl acetate=8+2). 1.9 g of 6-benzyloxy-3-bromoacetyl-4-methoxymethyl-9-tosyl-β-carboline is obtained. Melting point 165° C. (decomposition).

Workup

  1. customThe reaction mixture is evaporated to dryness
  2. washwashed with saturated NaCl solution
  3. customdried on Sikkon
  4. concentrationconcentrated by evaporation
  5. customThe crude product is chromatographed on silica gel (cyclohexane/ethyl acetate=8+2)

Sources & evidence

ORD record
ord-c41fbf7ff6334f41801dfa361bea5319
Source dataset
uspto-grants-1996_08
Patent number
US05543519

Reaction notes

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