Sodium Bicarbonate → HCID 86751323, compound

HRID 1379210Notes

Reaction equation

HRID 1379210 reaction equation
Cl.[CH3:2][N:3]([CH3:10])[CH2:4][CH2:5][CH2:6][C:7](O)=[O:8].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[F:34][C:35]([F:65])([F:64])[C:36]1[CH:37]=[C:38]([CH:57]=[C:58]([C:60]([F:63])([F:62])[F:61])[CH:59]=1)[C:39]([N:41]1[CH2:46][CH2:45][NH:44][CH2:43][C@H:42]1[CH2:47][C:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[NH:50][CH:49]=1)=[O:40].C(=O)(O)[O-].[Na+]>ClCCl>[F:63][C:60]([F:61])([F:62])[C:58]1[CH:57]=[C:38]([CH:37]=[C:36]([C:35]([F:34])([F:64])[F:65])[CH:59]=1)[C:39]([N:41]1[CH2:46][CH2:45][N:44]([C:7](=[O:8])[CH2:6][CH2:5][CH2:4][N:3]([CH3:10])[CH3:2])[CH2:43][C@H:42]1[CH2:47][C:48]1[C:56]2[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=2)[NH:50][CH:49]=1)=[O:40]

Participants

7

Reactant 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazineHCID 126916404-(Dimethylamino)butyric acid hydrochloride

Product 1

HCID 86751323HCID 86751323, compoundYield 105.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of 4-(dimethylamino)butyric acid hydrochloride (70 mg) and 1-hydroxybenzotriazole hydrate (160 mg) in dichloromethane (10 ml) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (80 mg) under ice cooling. After stirring for 30 minutes, a solution of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (200 mg) in dichloromethane (5 ml) was added at the same temperature. The resulting mixture was stirred for 2.5 hours at room temperature. Dichloromethane and aqueous sodium bicarbonate solution were added to the reaction mixture and then the organic layer was separated and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-[4-(dimethylamino)butyryl]-2-(1H-indol-3-yl-methyl)piperazine (0.25 g).

Workup

  1. stirringThe resulting mixture was stirred for 2.5 hours at room temperature
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-ae08e38883f5499f802770542e4e67e6
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Reaction notes

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