Benzyl Bromide → HCID 59382283, compound

HRID 425186Notes

Reaction equation

HRID 425186 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]([C:39]([CH3:41])=[CH2:40])=[CH:27][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:44](Br)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>CN(C=O)C.CCOC(C)=O.O>[CH2:44]([N:13]([C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:18][CH:19]=1)[C:11](=[O:12])[C:10]1[CH:27]=[C:28]([C:39]([CH3:41])=[CH2:40])[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:30][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 667016982,4-Bis-benzyloxy-5-isopropenyl-N-(4-morpholin-4-ylmethyl-phenyl)-benzamide

Product 1

HCID 59382283HCID 59382283, compoundYield 69.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Bis-benzyloxy-5-isopropenyl-N-(4-morpholin-4-ylmethyl-phenyl)-benzamide (0.245 g, 0.45 mmol) [prepared using Method A2 from (2,4-bis-benzyloxy-5-isopropenyl)-benzoic acid (Preparation B5) and 4-morpholin-4-yl-methyl-phenylamine] dissolved in DMF (3 ml), was treated with 60% NaH in mineral oil (27 mg, 1.5 eq) and stirred for 15 minutes followed by the addition of benzyl bromide (0.052 ml, 0.45 mmol), then stirred for a further 2 hours at room temperature. The reaction was diluted with EtOAc and water. The EtOAc layer was separated, washed with brine, dried (MgSO4) and evaporated to afford 0.2 g of the title compound as a yellow oil. MS: [M+H]+ 639.

Workup

  1. stirringstirred for a further 2 hours at room temperature
  2. customThe EtOAc layer was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c03ae0f0500849d08af2c5fa83e00ab0
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

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