Hydrochloric Acid → N-[4-(3-Oxo-3-phenylpropyl)phenyl]acetamide

HRID 356471Notes

Reaction equation

HRID 356471 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])=[CH:11][CH:10]=1.CCN(CC)CC.Cl>CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:18]=[C:17]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:16][CH2:15][C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:1](=[O:3])[CH3:2])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 122630371-Propanone, 3-(4-aminophenyl)-1-phenyl-

Product 1

HCID 18798652N-[4-(3-Oxo-3-phenylpropyl)phenyl]acetamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (2.45 mL, 26 mmol) was added to a solution of 3-(4-amino-phenyl)-1-phenyl-propan-1-one from Example X (4.5 g, 20 mmol), NEt3 (3.1 mL, 22.2 mmol), and a crystal of DMAP in CH2Cl2 (50 mL). The reaction mixture was stirred overnight at room temperature, then poured onto 1N HCl. The product was partitioned between CH2 Cl2 and H2O, and the organic phase was dried (MgSO4) and concentrated to give the title compound. 1H NMR (CDCl3) δ 2.16 (s, 3 H), 3.03 (t, 2 H), 3.28 (t, 2 H), 7.20 (d, 2 H), 7.37-7.60 (m, 6 H), 7.94 (d, 2 H).

Workup

  1. customThe product was partitioned between CH2 Cl2 and H2O
  2. dry with materialthe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ec76d1ed413f4c4d8f1082164aaf510a
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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