Trityl chloride → HCID 53918913, compound

HRID 486785Notes

Reaction equation

HRID 486785 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][CH2:7][C@@H:6]3[CH2:12][C@@H:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:14][C:4]=1[C:5]=23)#[N:2].CCN(CC)CC.[C:29]1([C:35](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:35]([N:8]1[C:9]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[C:4]3[CH2:14][C@H:13]([N:15]([CH2:19][CH2:20][CH3:21])[CH2:16][CH2:17][CH3:18])[CH2:12][C@H:6]([C:5]=23)[CH2:7]1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 18652840HCID 18652840, compound

Product 1

HCID 53918913HCID 53918913, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a sol of (2aR,4R)-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole (1 g, 3.5 mmol) and Et3N (354 mg, 3.5 mmol) in 50 mL of methylene chloride was added a sol of triphenylmethyl chloride (trityl chloride) (0.98 g, 3.5 mmol) in 10 mL of methylene chloride dropwise at RT. The reaction mixture was stirred for 16 hr at RT. The reaction mixture was extracted with water and cold 1 N HCl. The organic sol was washed with sat'd NaHCO3 sol and with sat'd brine sol. The organic sol was dried (MgSO4) and conc to dryness in vacuo to give a residue. The residue was slurried with warm hexanes, cooled and filtered to remove insolubles. The filtrate was conc to an oil. The oil was chromatographed (silica gel, 20% EtOAc in hexanes) to provide 1.5 g of (2aR,4R)-1-trityl-6-cyano-4-(di-n-propylamino)-1,2,2a,3,4,5-hexahydrobenz[cd]indole.

Workup

  1. extractionThe reaction mixture was extracted with water and cold 1 N HCl
  2. washThe organic sol was washed with sat'd NaHCO3 sol and with sat'd brine sol. The organic sol
  3. dry with materialwas dried (MgSO4)
  4. customconc to dryness in vacuo to give a residue
  5. temperaturecooled
  6. filtrationfiltered
  7. customto remove insolubles
  8. customThe oil was chromatographed (silica gel, 20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-641e3b70dc994907895e1ab8c22e4dda
Source dataset
uspto-grants-1994_03
Patent number
US05292766

Reaction notes

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