Acetic Acid → 3-(Benzylamino-methyl)-benzoic acid methyl ester

HRID 418357

反応式

HRID 418357 の反応式
Cl.[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH2:12])[CH:6]=1.CC(O)=O.[CH:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[BH4-].[Na+]>ClC(Cl)C.CO>[CH3:2][O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=1

参加物

7

反応物 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 2794825Methyl 3-(aminomethyl)benzoate HydrochlorideHCID 4311764Sodium borohydride

生成物 1

HCID 591908593-(Benzylamino-methyl)-benzoic acid methyl ester収率 77.9%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒

反応条件

温度
120 °C

実験手順

Suspended 3-aminomethyl-benzoic acid methyl ester hydrochloride (100 mg. 0.99 mmol) in 3 mL of dichloroethane in a microwave tube and added 100 uL of AcOH. To this was added benzaldehyde (0.10 mL, 1.00 mmol). The mixture was sealed and heated at 120° C. for 20 minutes resulting in a homogeneous solution. 2 mL of MeOH was added and the mixture was treated with NaBH4 (56.8 mg, 1.50 mmol) resulting in gas evolution. The mixture stirred for 19 h. The mixture was quenched with careful addition of 5% HCl resulting in a bi-phasic mixture. The aqueous phase was removed and treated with 50×2-200 Dowex acidic ion exchange resin. The product was liberated with 10% NH3 in MeOH and concentrated to give 197 mg of 3-(benzylamino-methyl)-benzoic acid methyl ester, partially contaminated with starting benzyl amine (15%).

後処理

  1. customThe mixture was sealed
  2. customresulting in a homogeneous solution
  3. customresulting in gas evolution
  4. customThe mixture was quenched with careful addition of 5% HCl resulting in a bi-phasic mixture
  5. customThe aqueous phase was removed
  6. additiontreated with 50×2-200 Dowex acidic ion exchange resin
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1f7dce752bee41079aa1568231eb9191
出典データセット
uspto-grants-2012_01
特許番号
US08093266B2

関連ノート

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