Phenethylamine → N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide

HRID 749304Notes

Reaction equation

HRID 749304 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[C:12]([C:19](O)=O)[N:13]2[CH3:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN([C:25]([O:29]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH2:63]([NH2:71])[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C=O)C>[CH2:63]([NH:71][C:25]([CH2:19][C:12]1[N:13]([CH3:18])[C:14]2[C:10]([CH:11]=1)=[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH:17]=[CH:16][CH:15]=2)=[O:29])[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 47776784-Benzyloxy-1-methyl-1H-indole-2-carboxylic acid

Product 1

HCID 131725790N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-benzyloxy-1-methyl-1H-indole-2-carboxylic acid (0.20 g) in DMF (10 mL) was added TBTU (0.23 g), HOBt (0.11 g) and DIEA (0.27 mL). After 5 min., phenethylamine (0.11 mL) was added and stirring was continued overnight under nitrogen at room temperature. The residue remaining after DMF evaporation was dissolved in EtOAc; washed with dilute HCl, saturated NaHCO3, and brine; dried over MgSO4; and concentrated at reduced pressure to give the intermediate product N-phenethyl 4-benzyloxy-1-methyl-1H-indole-2-carboxyamide (0.18 g) which was used without further purification. Hydrogenation of this product by a method analogous to that described in Example 9 give 0.14 g of the title compound.

Workup

  1. waitwas continued overnight under nitrogen at room temperature
  2. customafter DMF evaporation
  3. dissolutionwas dissolved in EtOAc
  4. washwashed with dilute HCl, saturated NaHCO3, and brine
  5. dry with materialdried over MgSO4
  6. concentrationand concentrated at reduced pressure

Sources & evidence

ORD record
ord-d32f939899cb4a6bb5e5065127b0b33e
Source dataset
uspto-grants-2008_07
Patent number
US07402604B2

Reaction notes

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