Water → HCID 9851065, compound

HRID 1108653Notes

Reaction equation

HRID 1108653 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:38]=[CH:37][C:8]([CH2:9][N:10]2[C:22]3[C:21]4[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:20]=4[CH2:19][CH2:18][C:17]=3[C:16]3[C:11]2=[CH:12][CH:13]=[C:14]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:15]=3)=[CH:7][CH:6]=1.[NH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.O>CN(C=O)C>[CH3:28][O:27][C:25]1[CH:24]=[CH:23][C:21]2[C:22]3[N:10]([CH2:9][C:8]4[CH:37]=[CH:38][C:5]([O:4][CH2:3][CH2:2][N:39]5[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]5)=[CH:6][CH:7]=4)[C:11]4[C:16]([C:17]=3[CH2:18][CH2:19][C:20]=2[CH:26]=1)=[CH:15][C:14]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[CH:13][CH:12]=4

Participants

5

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 22118546HCID 22118546, compound

Product 1

HCID 9851065HCID 9851065, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

Intermediate #18, 11-[4-(2-Chloroethoxy)-benzyl]-8-benzyloxy-3-methoxy-5,11-dihydro-6H-benzo[a]carbazole, (6 g, 11.5 mmol) in DMF was treated with KI (2.5 g, 15.0 mmol) and piperidine (12 mL) and heated to 65° C. for 18 hours. The reaction was worked up by pouring the crude reaction mixture into water and extracting with ethyl acetate. The ethyl acetate layer was washed with NaHCO3 aq., brine and dried over MgSO4. The resultant was chromatographed on silica gel using CH2Cl2 (100%), CH2Cl2 :MeOH (98:2), CH2Cl2 :MeOH (96:4) as the eluting solvents. The product (3.2 g) was isolated as an oil: 1H NMR (DMSO) 7.52-7.12 (m, 8 H), 6.98-6.82 (m, 5 H), 6.80 (dd, 1 H, J=8.4 Hz, 2.6 Hz), 6.73 (dd, 1 H, J=8.8 Hz, 2.4 Hz), 5.56 (s, 2 H), 5.11 (s, 2 H), 3.98 (t, 2 H, J=6.0 Hz), 3.70 (s, 3 H), 2.85-2.78 (m, 2 H), 2.75 (s, 2 H), 2.60 (t, 2 H, J=6.5 Hz), 2.42-2.38 (m, 4 H), 1.70-1.58 (m, 4 H), 1.58-1.35 (m, 2 H).

Workup

  1. additionby pouring the crude
  2. extractionextracting with ethyl acetate
  3. washThe ethyl acetate layer was washed with NaHCO3 aq., brine
  4. dry with materialdried over MgSO4
  5. customThe resultant was chromatographed on silica gel

Sources & evidence

ORD record
ord-878c41854df8465986cb8e7680563314
Source dataset
uspto-grants-2000_05
Patent number
US06069153

Reaction notes

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