Hydrochloric Acid → HCID 22128097, compound

HRID 1005034Notes

Reaction equation

HRID 1005034 reaction equation
O[CH:2]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH:14]2[O:26][CH2:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C.[C:51](Cl)(=[O:58])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.Cl.C[OH:62]>CN(C)C1C=CN=CC=1.O.C(Cl)Cl>[C:51]([O:58][CH:2]([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]2[O:26][CH2:27][C:28]2[CH:37]=[CH:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=2)=[CH:11][CH:12]=1)(=[O:62])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 86604406HCID 86604406, compound

Product 1

HCID 22128097HCID 22128097, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 30 mg (0.052 mmol) of tert-butyl (3RS,4RS)-4-[4-(4-hydroxy-4-phenyl-butoxy)-phenyl]-3-naphthalen-2-ylmethoxy-piperidine-1-carboxylate (configuration unknown in the butoxy part), 25.5 gl (0.186 mmol, 3.6 eq.) of triethylamine and 1.7 ml of methylene chloride was treated in succession with 21.6 gl (0.186 mmol, 3.6 eq.) of benzoyl chloride and 2 mg (0.01 6 mmol) of 4-dimethylaminopyridine. This reaction solution was stirred at room temperature for 10 hours, then poured into 5 ml of water and extracted three times with 10 ml of ethyl acetate each time. The combined organic phases were dried over magnesium sulphate, evaporated under reduced pressure and dried in a high vacuum. The light yellow resin (62 mg) was dissolved in 1 ml of methanol, again concentrated, dried in a high vacuum. Without further purification and characterization the product obtained was reacted with hydrogen chloride in methanol analogously to the procedure described in Example 22(l). The brown-yellow resin (56 mg) was separated on silica gel using a 95:5 mixture of methylene chloride and methanol (extracted against 5 vol. % conc. ammonia) as the eluent. There were obtained 15 mg (50% of theory) of 4-[4-[(3RS,4RS)-3-naphthalen-2-ylmethoxy-piperidin-4-yl]-phenoxy]-1-phenyl-butyl benzoate (configuration unknown in the butoxy part) as a colourless resin; MS: 586 (M+H)+.

Workup

  1. extractionextracted three times with 10 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over magnesium sulphate
  3. customevaporated under reduced pressure
  4. customdried in a high vacuum
  5. dissolutionThe light yellow resin (62 mg) was dissolved in 1 ml of methanol
  6. concentrationagain concentrated
  7. customdried in a high vacuum
  8. customWithout further purification and characterization the product
  9. customobtained
  10. customThe brown-yellow resin (56 mg) was separated on silica gel using
  11. additiona 95:5 mixture of methylene chloride and methanol (extracted against 5 vol. % conc. ammonia) as the eluent

Sources & evidence

ORD record
ord-23bb71672d604adab547960a8f50709b
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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