Dimethylamine, hydrochloride → HCID 15230490, compound

HRID 274799Notes

Reaction equation

HRID 274799 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[CH2:11][C:10](=O)[CH2:9][CH2:8]2)#[N:2].Cl.[CH3:15][NH:16][CH3:17].C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>C(#N)C.[OH-].[NH4+]>[CH3:15][N:16]([CH3:17])[CH:10]1[CH2:9][CH2:8][C:7]2[C:12](=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=2)[CH2:11]1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 15230502HCID 15230502, compound

Product 1

HCID 15230490HCID 15230490, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14923Ammonium HydroxideSolvent

Procedure

8-Cyano-2-tetralone (2 gm, 11.7 mMol) in acetonitrile (30 mL) with dimethylamine hydrochloride (5.72 gm, 70 mMol), sodium acetate (5.76 gm, 70 mMol), sodium cyanoborohydride (520 mg, 8.2 mMol) and 3A molecular sieves (1.2 gm) were stirred together for 4 days at room temperature. The reaction mixture was then diluted with conc. ammonium hydroxide and stirred for 4 hours. This mixture was extracted with dichloromethane. The organic extracts were combined, dried over sodium sulfate and concentrated in vacuo to give a dark oil. Purification on a basic alumina column (Activity I, 2% methanol in dichloromethane) gave a brown oil which was converted to its hydrochloride salt. Recrystallization (methanol/diethyl ether) gave colorless crystals (520 mg, m.p.=229°-230° C.).

Workup

  1. extractionThis mixture was extracted with dichloromethane
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customto give a dark oil
  5. customPurification on a basic alumina column (Activity I, 2% methanol in dichloromethane)
  6. customgave a brown oil which
  7. customRecrystallization (methanol/diethyl ether)

Sources & evidence

ORD record
ord-7cd3cf685df64d30a48c3b5312f275c3
Source dataset
uspto-grants-1995_02
Patent number
US05389687

Reaction notes

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