Phenethyl bromide → HCID 44434069, compound

HRID 130807Notes

Reaction equation

HRID 130807 reaction equation
[CH2:1]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)=[CH:11][C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].Br[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C=O)C>[CH2:29]([N:3]1[CH2:4][CH2:5][C:6]2[CH:11]=[C:10]([O:12][C:13]3[CH:21]=[CH:20][C:16]([C:17]([NH2:19])=[O:18])=[CH:15][N:14]=3)[CH:9]=[CH:8][C:7]=2[CH2:1][CH2:2]1)[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7666Phenethyl bromideHCID 11430Potassium CarbonateHCID 59730149HCID 59730149, compound

Product 1

HCID 44434069HCID 44434069, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Take up 6-(2,3,4,5-tetrahydro-1H-benzo[d]azepin-7-yloxy)nicotinamide (0.0500 g, 0.176 mmol) and K2CO3 (0.0488 g, 0.353 mmol) in DMF (1.0 mL). Add 2-bromoethylbenzene (0.0265 mL, 0.194 mmol) and heat to 70° C. overnight. Remove DMF as an azeotrope with xylenes. Purify by 5 g SCX column by washing with methanol and eluting with 2.0 M NH3 in methanol. Then purify by flash chromatography, eluting with 0-10% ethyl acetate and 5% (2.0 M NH3 in methanol) in dichloromethane to give the title compound: MS ES+ 388.1 (M+H)+; HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 30-99% over 19 min], tR=1.7 min, 100% purity.

Workup

  1. customPurify by 5 g SCX column
  2. washby washing with methanol
  3. washeluting with 2.0 M NH3 in methanol
  4. customThen purify by flash chromatography
  5. washeluting with 0-10% ethyl acetate and 5% (2.0 M NH3 in methanol) in dichloromethane

Sources & evidence

ORD record
ord-019214c0700c41508615020c664b1533
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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