Hydrochloric Acid → HCID 53796003, compound

HRID 1816708Notes

Reaction equation

HRID 1816708 reaction equation
[CH2:1]([S:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([N:17]3[CH2:22][CH2:21][N:20]([C:23]4[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=4)[CH2:19][CH2:18]3)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH3:3].O[N:33]1[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[N:34]1.Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.C(N(CC)CC)C>[N:33]1([O:28][C:27](=[O:29])[C:26]2[CH:25]=[CH:24][C:23]([N:20]3[CH2:19][CH2:18][N:17]([C:14]4[CH:13]=[CH:12][C:11]([N:8]5[CH2:7][CH2:6][CH:5]([S:4][CH2:1][CH2:2][CH3:3])[CH2:10][CH2:9]5)=[CH:16][CH:15]=4)[CH2:22][CH2:21]3)=[CH:31][CH:30]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=2[N:35]=[N:34]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22494632HCID 22494632, compound

Product 1

HCID 53796003HCID 53796003, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[1-[4-(4-propylthiopiperidin-1-yl)phenyl]piperazin-4-yl]benzoic acid (0.98 g), 1-hydroxybenzotriazole (0.39 g) in dichloromethane (20 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (WSCD.HCl) (0.85 g), and the mixture was stirred for 15 minutes. To the solution was added triethylamine (0.31 ml), and the mixture was stirred overnight at ambient temperature. The reaction mixture was poured into a mixture of 0.1N-hydrochloric acid (25 ml) and dichloromethane (60 ml). The organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. To the resulting precipitates were washed with water and IPE (50 ml), collected by filtration and dried under reduced pressure to give 4-[1-[4-(4-propylthiopiperidin-1-yl)phenyl)piperazin-4-yl]benzoic acid benzotriazol-1-yl ester (1.04 g).

Workup

  1. stirringthe mixture was stirred overnight at ambient temperature
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customTo the resulting precipitates
  6. washwere washed with water and IPE (50 ml)
  7. filtrationcollected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-ebbeec7ef2c84edbaed74b40ebb387f5
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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