Dichloromethane → HCID 178483392, compound

HRID 1884518Notes

Reaction equation

HRID 1884518 reaction equation
[C:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([NH:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25](Cl)Cl.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>CO>[CH3:25][N:13]([C@H:10]1[CH2:11][CH2:12][C@H:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9]1)[CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 178516010HCID 178516010, compound

Product 1

HCID 178483392HCID 178483392, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of trans-4-[4-(4-phenylcyclohexylamino)-butyl]phenol (370 mg, 1.1 mmol) in a mixture of MeOH (5 mL) H2O (0.5 mL), and CH2Cl2 (5 mL) was added ρformaldehyde (170 mg, 5.7 mmol). After stirring for 10 minutes, NaBH(OAc)3 (300 mg, 1.4 mmol) was added, and the reaction mixture was stirred for 12 hours. Solid NaOH was added to give a clear solution, which was then concentrated under reduced pressure. Purification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH) and formation of the HCl salt gave (b) trans-4-{4-[methyl-(4-phenylcyclohexyl)amino]butyl}-phenol (230 mg, 56%), as a white solid: mp 234-236° C.; IR (KBr): 2942, 1613, 1515 cm−1; 1H NMR (500 MHz, DMSO-d6) δ 9.96 (br s, 1H), 9.13 (s, 1H), 7.31-7.18 (m, 5H), 7.00 (d, J=8.5 Hz, 2H), 6.68(d, J=8.5 Hz, 2H), 3.33-3.23 (m, 1H), 3.17-3.09 (m, 1H), 3.02-2.95 (m, 1H), 2.67(d, J=5 Hz, 3H), 2.55-2.49 (m, 3H), 2.16-2.06 (m, 2H), 1.95-1.89 (m, 2H), 1.72-1.50 (m, 8H); CI—MS (methane) (m/z): 338 [M+H]+; HPLC: method A, 6.38 minutes (>99%); method B, 11.28 minutes (>99%); Anal. Calcd for C23H31NO.HCl: C, 73.87; H, 8.62; N, 3.75. Found: C, 73.61; H, 8.55; N, 3.66.

Workup

  1. additionwas added ρformaldehyde (170 mg, 5.7 mmol)
  2. stirringthe reaction mixture was stirred for 12 hours
  3. customto give a clear solution, which
  4. concentrationwas then concentrated under reduced pressure
  5. customPurification by flash chromatography (silica, 89:10:1 CH2Cl2:MeOH:NH4OH) and formation of the HCl salt

Sources & evidence

ORD record
ord-c24599530d804908a28950ace2783165
Source dataset
uspto-grants-2004_07
Patent number
US06765022B2

Reaction notes

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