3-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamine → HCID 20559441, compound

HRID 224652Notes

Reaction equation

HRID 224652 reaction equation
[N:1]([CH2:4][CH2:5][S:6][CH2:7][C:8]1[O:12][C:11]([CH2:13][N:14]([CH3:16])[CH3:15])=[CH:10][CH:9]=1)=[C:2]=[S:3].[NH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]([CH2:28][N:29]([CH3:31])[CH3:30])[CH:25]=[CH:26][CH:27]=1>C(#N)C>[CH3:15][N:14]([CH2:13][C:11]1[O:12][C:8]([CH2:7][S:6][CH2:5][CH2:4][NH:1][C:2]([NH:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]([CH3:30])[CH3:31])[CH:23]=2)=[S:3])=[CH:9][CH:10]=1)[CH3:16]

Participants

4

Reactant 2

HCID 129139503-(3-Aminopropoxy)-N,N-dimethylbenzenemethanamineHCID 20513971N,N-dimethyl-5-[[[2-(isothiocyanato)ethyl]thio]methyl]furanmethanamine

Product 1

HCID 20559441HCID 20559441, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 5-[[[2-(isothiocyanato)ethyl]thio]methyl]-N,N-dimethyl-2-furanmethanamine (0.77 g) in dry acetonitrile (3 ml) was added a solution of 3-(3-aminopropoxy)-N,N-dimethylbenzenemethanamine (0.63 g) in dry acetonitrile (3 ml). After 1 hour the solution was evaporated to dryness to give an oil which was chromatographed (silica/methanol-0.88 ammonia 79:1). The appropriate eluate was evaporated to dryness to give the title compound (1.25 g) as an oil.

Workup

  1. customAfter 1 hour the solution was evaporated to dryness
  2. customto give an oil which
  3. customwas chromatographed (silica/methanol-0.88 ammonia 79:1)
  4. customThe appropriate eluate was evaporated to dryness

Sources & evidence

ORD record
ord-70aec4e2dcc44d299dd511f256616529
Source dataset
uspto-grants-1980_11
Patent number
US04233302

Reaction notes

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