Aniline → 3-Phenylaminomethyl-azepane-1-carboxylic acid benzyl ester

HRID 1839220Notes

Reaction equation

HRID 1839220 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([CH:25]=O)[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH3-]C#N.[Na+]>CC(O)=O.CO>[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([CH2:25][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 20598085Benzyl 3-formylazepane-1-carboxylate

Product 1

HCID 205980843-Phenylaminomethyl-azepane-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Aniline (0.126 mL, 1.38 mmol) was added to a solution of 3-formyl-azepane-1-carboxylic acid benzyl ester (147) (0.300 g, 1.15 mmol) in 5% HOAc in MeOH (11.5 mL). The reaction was stirred for approx. 20 minutes, then NaBH3CN (0.2164 g, 3.44 mmol) was slowly added and the reaction was stirred at room temperature overnight. The reaction was then concentrated in vacuo and EtOAc and a few drops of 10% NaOH were added. The organic was washed with saturated NaCl (aq), dried with NaSO4, concentrated in vacuo, to give crude 3-phenylaminomethyl-azepane-1-carboxylic acid benzyl ester (148). Compound 148 was used in the next step without further purification.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. concentrationThe reaction was then concentrated in vacuo and EtOAc and a few drops of 10% NaOH
  3. additionwere added
  4. washThe organic was washed with saturated NaCl (aq)
  5. dry with materialdried with NaSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c94a0d9c4364bd180f419607b052581
Source dataset
uspto-grants-2004_01
Patent number
US06677332B1

Reaction notes

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