Sodium Hydroxide → [2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-amine

HRID 553278Notes

Reaction equation

HRID 553278 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][NH2:11].[I:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][CH2:10][NH:11][CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[C:13]([I:12])[CH:14]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 2526103-IodobenzaldehydeHCID 27341012,6-DichlorophenethylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67165340[2-(2,6-Dichloro-phenyl)-ethyl]-(3-iodo-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2,6-Dichlorophenyl)ethylamine (1.0 g) and 3-iodobenzaldehyde (1.2 g) were combined in dichloromethane (50 mL). After 1 hour, sodium triacetoxyborohydride (2.2 g) was added. After 3.5 hours, the reaction mixture was poured onto 1M aqueous sodium hydroxide (200 mL) and extracted twice with dichloromethane. The organics were combined, dried (sodium sulfate) and evaporated to give the subtitle product, as an oil (2.0 g).

Workup

  1. waitAfter 3.5 hours
  2. extractionextracted twice with dichloromethane
  3. dry with materialdried (sodium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-720d2176a94d4355b57a62aadba8e50a
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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