Triethylamine → N-[2-benzyloxy-4-(2-dipropylaminoethyl)phenyl]butyramide

HRID 1032539Notes

Reaction equation

HRID 1032539 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[CH:11][C:10]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:32](Cl)(=[O:36])[CH2:33][CH2:34][CH3:35]>O1CCCC1.O>[CH2:25]([O:24][C:10]1[CH:11]=[C:12]([CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])[CH:13]=[CH:14][C:9]=1[NH:8][C:32](=[O:36])[CH2:33][CH2:34][CH3:35])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 22165977HCID 22165977, compound

Product 1

HCID 22166027N-[2-benzyloxy-4-(2-dipropylaminoethyl)phenyl]butyramide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.3 ml of triethylamine is added to 0.65 g of N-[2-(4-amino-3-benzyloxyphenyl)ethyl]-N,N-dipropylamine in 10 ml of tetrahydrofuran, and then 0.23 ml of butyryl chloride is added dropwise thereto. The reaction mixture is stirred for one hour at room temperature, diluted with water, and the product extracted by shaking with methylene chloride, isolating 770 mg of N-[2-benzyloxy-4-(2-dipropylaminoethyl)phenyl]butyramide as an oil from the methylene chloride solution.

Workup

  1. extractionthe product extracted
  2. stirringby shaking with methylene chloride

Sources & evidence

ORD record
ord-4356bc771a284de6a5842a169bffc404
Source dataset
uspto-grants-1990_09
Patent number
US04958026

Reaction notes

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