7-Methoxy-2-tetralone → (1-Benzyl-piperidin-4-yl)-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine

HRID 393201Notes

Reaction equation

HRID 393201 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][C:9](=O)[CH2:10]2)=[CH:5][CH:4]=1.[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH2:14]([N:21]1[CH2:26][CH2:25][CH:24]([NH:27][CH:9]2[CH2:8][CH2:7][C:6]3[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:10]2)[CH2:23][CH2:22]1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 777857-Methoxy-2-tetraloneHCID 4158521-Benzyl-4-piperidylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 12135180(1-Benzyl-piperidin-4-yl)-(7-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl)-amine

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one (10 g, 56.7 mmol) and 1-benzyl-piperidin-4-ylamine (12.7 mL, 62.4 mmol) in dichloroethane (50 mL) under a nitrogen atmosphere was added sodium triacetoxyborohydride (30 g, 141.8 mmol, 3.5 eq.) in a single portion. The reaction was stirred at room temperature for 24 h. The reaction was concentrated in vacuo and partitioned between EtOAc (100 mL) and 5% aq. KOH (50 mL). The aqueous layer was extracted twice more with EtOAc (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated to afford a dark oil. This material was used directly in Step 2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompartitioned between EtOAc (100 mL) and 5% aq. KOH (50 mL)
  3. extractionThe aqueous layer was extracted twice more with EtOAc (2×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a dark oil

Sources & evidence

ORD record
ord-60d8719a77e845f0928c90ed32c4b943
Source dataset
uspto-grants-2004_10
Patent number
US06806278B2

Reaction notes

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