Triethylamine → HCID 70248516, compound

HRID 650962Notes

Reaction equation

HRID 650962 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[C:11]2[CH:6]([CH2:7][CH2:8][N:9]([CH3:14])[CH:10]2[CH3:13])[CH2:5][CH:4]=1.[Br:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][C:24]=1[CH2:25][CH3:26])[C:19](Cl)=[O:20].C(N(CC)CC)C>ClCCl>[CH3:13][CH:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([NH:2][C:19](=[O:20])[C:18]3[CH:22]=[CH:23][C:24]([CH2:25][CH3:26])=[C:16]([Br:15])[CH:17]=3)[CH:12]=2)[CH2:7][CH2:8][N:9]1[CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21710461HCID 21710461, compoundHCID 86757258HCID 86757258, compound

Product 1

HCID 70248516HCID 70248516, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(±) 7-Amino-1,2-dimethyl-tetrahydroisoquinoline mono hydrochloride (0.106 g, 0.50 mmol) in dichloromethane (10 ml) was sequentially treated with 3-bromo-4-ethylbenzoyl chloride (0.124 g, 0.50 mmol) and triethylamine (0.3 ml, 2.2 mmol). The mixture was stirred at ambient temperature for 18 h. Evaporation in vacuo gave an oily residue which was purified by chromatography through silica gel eluting with (0.5% conc. ammonia: 4.5% methanol: 95% dichloromethane). The title compound was obtained as an off-white foam (0.149 g, 77%).

Workup

  1. customEvaporation in vacuo
  2. customgave an oily residue which
  3. customwas purified by chromatography through silica gel eluting with (0.5% conc. ammonia: 4.5% methanol: 95% dichloromethane)

Sources & evidence

ORD record
ord-46ebcf568525483480aa62c3dda1a487
Source dataset
uspto-grants-2001_08
Patent number
US06277861B1

Reaction notes

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