6-Methoxy-2-naphthaldehyde → 1-(1-(3-Chlorophenyl)-2-[4-[(6-methoxy-2-naphthyl)methyl]piperazin-1-yl]ethyl)cyclohexanol dihydrochloride

HRID 1987409Notes

Reaction equation

HRID 1987409 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:16]2([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:9][N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[CH:31]=[C:30]([CH:35]=O)[CH:29]=[CH:28]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([C:16]2([OH:22])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([CH2:35][C:30]3[CH:29]=[CH:28][C:27]4[C:32](=[CH:33][CH:34]=[C:25]([O:24][CH3:23])[CH:26]=4)[CH:31]=3)[CH2:12][CH2:11]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 769916-Methoxy-2-naphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 103815021-[1-(3-Chlorophenyl)-2-piperazin-1-ylethyl]cyclohexanol

Product 1

HCID 113305071-(1-(3-Chlorophenyl)-2-[4-[(6-methoxy-2-naphthyl)methyl]piperazin-1-yl]ethyl)cyclohexanol dihydrochlorideYield 165.8%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

A solution of 1-[1-(3-chlorophenyl)-2-piperazin-1-ylethyl]cyclohexanol (see Example 1) (200 mg, 0.62 mmol) and 6-methoxy-2-napthaldehyde (173 mg, 0.93 mmol) in dichloroethane (4 mL) was treated with sodium trisacetoxyborohydride (195 mg, 0.92 mmol). The reaction was placed on a shaker and where it was stirred for 16 h. The reaction was then washed with a 2 N aqueous solution of hydrochloric acid (2×2 mL), and the organic layer was stored at 25° C. for 16 h. The resulting precipitate was collected, washed with diethyl ether and dried in vacuo to yield 194 mg (64%) 1-(1-(3-chlorophenyl)-2-[4-[(6-methoxy-2-naphthyl)methyl]piperazin-1-yl]ethyl)cyclohexanol dihydrochloride as a white solid. MS (ESI) m/z 493/495 ([M+H]+); HRMS: calcd for C30H37ClN2O2.2.00 HCl, 564.2077. found (ESI_FT), 493.2632.

Workup

  1. washThe reaction was then washed with a 2 N aqueous solution of hydrochloric acid (2×2 mL)
  2. waitthe organic layer was stored at 25° C. for 16 h
  3. customThe resulting precipitate was collected
  4. washwashed with diethyl ether
  5. customdried in vacuo

Sources & evidence

ORD record
ord-bfdb798e1b5b461d9df019a014dc7958
Source dataset
uspto-grants-2009_06
Patent number
US07550485B2

Reaction notes

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