Benzenepropanal → HCID 18445296, compound

HRID 459930Notes

Reaction equation

HRID 459930 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][CH:5]([O:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.[C:18]1([CH2:24][CH2:25][CH:26]=O)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C>C(Cl)Cl>[C:18]1([CH2:24][CH2:25][CH2:26][N:2]2[CH2:3][CH2:4][CH:5]([O:8][C:9]3[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[O:14])=[CH:11][CH:10]=3)[CH2:6][CH2:7]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7707BenzenepropanalHCID 2724942TriacetoxyborohydrideHCID 184453054-(Piperidin-4-yloxy)benzamide hydrochloride

Product 1

HCID 18445296HCID 18445296, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Combine 4-(piperidin-4-yloxy)-benzamide hydrochloride (102 mg, 0.397 mmol), 3-phenyl-propionaldehyde (106 μL, 0.796 mmol) and triacetoxy-borohydride (127 mg, 0.597 mmol) in CH2Cl2 (3 mL). Stir the reaction mixture at room temperature overnight. Dilute the reaction mixture with CH2Cl2 (3 mL) and wash with sodium hydroxide (1N, aq. 5 mL). Separate the organic layer and placed onto an SCX column directly eluting with ammonia (2.0 in methanol). The resulting residue was triturated with CH2Cl2 and diethyl ether to provide the title compound (63 mg, 47%) as a white solid. mass spectrum (ion spray): m/z=339.1 (M+1); 1H NMR (CDCl3): 7.79 (ad, J=9.0 Hz, 3H), 7.28–7.12 (m, 6H), 6.95 (d, J=9.0 Hz, 2H), 4.74–4.40 (m, 1H), 2.70–2.63 (bm, 2H), 2.56 (t, J=7.6 Hz, 2H), 2.31–2.25 (bm, 2H), 2.22–2.15 (bm, 2H), 1.96–1.89 (bm, 2H), 1.71 (pentet, J=7.3 Hz, 2H), 1.63–1.56 (m, 2H).

Workup

  1. washwash with sodium hydroxide (1N, aq. 5 mL)
  2. customSeparate the organic layer
  3. washdirectly eluting with ammonia (2.0 in methanol)
  4. customThe resulting residue was triturated with CH2Cl2 and diethyl ether

Sources & evidence

ORD record
ord-bc67517d975c4e5fa98137db333903f8
Source dataset
uspto-grants-2007_03
Patent number
US07196100B2

Reaction notes

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