Dimethylamine, hydrochloride → HCID 57068080, compound

HRID 2299692Notes

Reaction equation

HRID 2299692 reaction equation
C(OC([N:8]([CH:20]1[CH2:26][C:25]2[CH:27]=[C:28]([O:31][CH2:32][C:33]([OH:35])=O)[CH:29]=[CH:30][C:24]=2[CH2:23][CH2:22][CH2:21]1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O)(C)(C)C.[CH3:36][N:37](C)[CH2:38]CCN=C=NCC.Cl.CNC>ClCCl.C(OCC)(=O)C>[OH:19][C@H:10]([CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:9][NH:8][CH:20]1[CH2:26][C:25]2[CH:27]=[C:28]([O:31][CH2:32][C:33]([N:37]([CH3:38])[CH3:36])=[O:35])[CH:29]=[CH:30][C:24]=2[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 57108693HCID 57108693, compound

Product 1

HCID 57068080HCID 57068080, compoundYield 58.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[8-[N-tert-butoxycarbonyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid (200 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (122 mg) and 1-hydroxyenzotriazole hydrate (66 mg) in dichloromethane (20 ml) was added dimethylamine hydrochloride (38.4 mg), and the mixture was stirred at room temperature for 18 hours. The resulting mixture was diluted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel and treated with 4N hydrogen chloride in ethyl acetate to afford 2-[8-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-N,N-dimethylacetamide (100 mg).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel
  5. additiontreated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-ad8444462fde43caa598b53e4e74b036
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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