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

HRID 1003825Notes

Reaction equation

HRID 1003825 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 CH2Cl2 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 CH2Cl2 and H2O
  2. dry with materialthe organic phase was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-734a99be82a34043a4c4f842fa8295e4
Source dataset
uspto-grants-2000_04
Patent number
US06046355

Reaction notes

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