1,4-Dibromobutane → HCID 57467339, compound

HRID 510544Notes

Reaction equation

HRID 510544 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[NH2:18].Br[CH2:23][CH2:24][CH2:25][CH2:26]Br.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][CH:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH2:9][CH2:8][CH:7]1[N:18]1[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 8471TriethylamineHCID 68513086HCID 68513086, compound

Product 1

HCID 57467339HCID 57467339, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(3-Chlorobenzyl)-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine (6 g, 19.88 mmol) was dissolved in acetonitrile (150 mL). 1,4-Dibromobutane (2.61 mL, 21.87 mmol) and triethylamine (6.1 mL, 43.7 mmol) were added and the reaction mixture heated under reflux for 3 h. The reaction mixture was poured on ice and extracted with dichloromethane. The combined organic extracts were successively washed with water and brine, dried (MgSO4) and the solvent was evaporated in vacuo. The crude product (6.6 g) was used for the next step without further purification.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureunder reflux for 3 h
  3. additionThe reaction mixture was poured on ice
  4. extractionextracted with dichloromethane
  5. washThe combined organic extracts were successively washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customthe solvent was evaporated in vacuo
  8. customThe crude product (6.6 g) was used for the next step without further purification

Sources & evidence

ORD record
ord-75c3d5b6f18f458f847332d24770d4e7
Source dataset
uspto-grants-2015_08
Patent number
US09096619B2

Reaction notes

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