2-Isopropylaniline → HCID 66935667, compound

HRID 1028212Notes

Reaction equation

HRID 1028212 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH:13]([C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18])([CH3:15])[CH3:14].[NH2:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[CH2:30][N:29]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:28][CH2:27]2>C(N(CC)CC)C.ClCCl>[C:37]([O:36][C:34]([N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][CH:33]=[C:24]([NH:23][C:2]([NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=3[CH:13]([CH3:15])[CH3:14])=[O:4])[CH:25]=2)[CH2:30]1)=[O:35])([CH3:40])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 125612-IsopropylanilineHCID 94429TriphosgeneHCID 27563716-Amino-2-N-Boc-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 66935667HCID 66935667, compoundYield 201.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent2×

Procedure

To a dichloromethane (10 mL) solution of triphosgene (474 mg), a dichloromethane (10 mL) solution of 2-isopropylaniline (540 mg) and triethylamine (1.2 mL) was gradually added at room temperature. After 2 hours, a dichloromethane (10 mL) solution of 6-amino-2N-Boc-1,2,3,4-tetrahydroisoquinoline (993 mg) and triethylamine (1.2 mL) was added thereto. The reaction mixture was stirred for 30 minutes and concentrated. The residue was purified by chromatography (dichloromethane/ethyl acetate) to obtain the title compound (1.32 g, 81%) as an off-white solid.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography (dichloromethane/ethyl acetate)

Sources & evidence

ORD record
ord-f3f332458a874d3eb62c229db23e2368
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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