N,N-Dimethylglycine → HCID 178483916, compound

HRID 1255499Notes

Reaction equation

HRID 1255499 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]3[C:11](=[N:12][N:13]=[C:14]3[C@H:16]3[CH2:21][CH2:20][C@H:19]([O:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][CH2:17]3)[CH2:10][NH:9][CH2:8][C:7]=2[CH:29]=1.C(N(CC)CC)C.[CH3:37][N:38]([CH3:43])[CH2:39][C:40](O)=[O:41].Cl.CN(C)CCCN=C=NCC>O1CCCC1>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]2[N:15]3[C:11](=[N:12][N:13]=[C:14]3[C@H:16]3[CH2:17][CH2:18][C@H:19]([O:22][C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[CH2:20][CH2:21]3)[CH2:10][N:9]([C:40](=[O:41])[CH2:39][N:38]([CH3:43])[CH3:37])[CH2:8][C:7]=2[CH:29]=1

Participants

6

Reactant 4

HCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178478523HCID 178478523, compound

Product 1

HCID 178483916HCID 178483916, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of trans-8-chloro-1-(4-phenoxy-cyclohexyl)-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzoazulene hydrochloride (0.179 g, 0.41 mmol) in tetrahydrofuran (2 ml) was added triethylamine (0.058 ml, 0.41 mmol). The suspension was stirred for 10 minutes. The ammonium salts were removed by filtration. The filtrate was concentrated in vacuo. The residue was redissolved in tetrahydrofuran (3 ml) followed by consecutive addition of N,N-dimethylglycine (0.056 g, 0.54 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.104 g, 0.54 mmol Stirring for 18 h at 50° C. was followed by partitioning between water (50 ml) and dichloromethane (50 ml). The organic layer was separated. The aqueous layer was extracted with one 50-ml portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.057 g, 28%) as white solid.

Workup

  1. customThe ammonium salts were removed by filtration
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionThe residue was redissolved in tetrahydrofuran (3 ml)
  4. stirringStirring for 18 h at 50° C.
  5. customby partitioning between water (50 ml) and dichloromethane (50 ml)
  6. customThe organic layer was separated
  7. extractionThe aqueous layer was extracted with one 50-ml portion of dichloromethane
  8. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification by flash-chromatography with n-heptane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-ac6fc02eac2b439a9726ae7bf267b9d1
Source dataset
uspto-grants-2013_06
Patent number
US08461152B2

Reaction notes

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