Sodium Hydroxide → HCID 86753897, compound

HRID 1418573Notes

Reaction equation

HRID 1418573 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:26])/[CH:15]=[CH:16]/[C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH2:10][C@H:9]1[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)=[O:7].[OH-].[Na+].Cl.[CH3:49][N:50]([CH3:54])[CH2:51][CH2:52][Cl:53]>[Br-].C([N+](C)(C)C)CCCCCCCCCCCCCCC.ClCCl>[ClH:53].[F:45][C:2]([F:44])([F:1])[C:3]1[CH:4]=[C:5]([CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:39]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:26])/[CH:15]=[CH:16]/[C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)[CH2:10][C@H:9]1[CH2:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]([CH2:52][CH2:51][N:50]([CH3:54])[CH3:49])[CH:29]=1)=[O:7]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 86753899HCID 86753899, compound

Product 1

HCID 86753897HCID 86753897, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-yl-methyl)-4-(4-nitro-trans-cinnamoyl)piperazine (100 mg), powdered sodium hydroxide (30 mg) and cetyltrimethylammonium bromide (10 mg) in dichloromethane (2 ml) was added 2-dimethylaminoethyl chloride hydrochloride (50 mg) at room temperature. The resulting mixture was stirred at the same temperature for 14 hours. After adding dichloromethane (10 ml), the reaction mixture was filtered through Celite pad and the filtrate was concentrated in vacuo. The resulting residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (30:1) and then treated with 4N hydrogen chloride in ethyl acetate solution to give (2R)-1-[3,5-bis(-trifluoromethyl)benzoyl]-2-[1-(2-dimethylaminoethyl)-1H-indol-3-yl-methyl]-4-(4-nitro-trans-cinnamoyl)piperazine hydrochloride (34 mg).

Workup

  1. filtrationthe reaction mixture was filtered through Celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting residue was purified by column chromatography on a silica gel eluting with a mixture of dichloromethane and methanol (30:1)
  4. additiontreated with 4N hydrogen chloride in ethyl acetate solution

Sources & evidence

ORD record
ord-ef7a2cf7c14f4fab9d7c87f23a1a9ac5
Source dataset
uspto-grants-1999_03
Patent number
US05883098

Reaction notes

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