Dichloromethane → HCID 65275388, compound

HRID 423689Notes

Reaction equation

HRID 423689 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]1.Br[C:10]1[S:14][N:13]=[C:12]([CH:15]([CH3:17])[CH3:16])[N:11]=1.C(N(CC)CC)C.C(Cl)Cl>O>[CH3:16][CH:15]([C:12]1[N:11]=[C:10]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][OH:8])[CH2:3][CH2:2]2)[S:14][N:13]=1)[CH3:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 4207714-Piperidinemethanol2×HCID 53408113HCID 53408113, compound

Product 1

HCID 65275388HCID 65275388, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-piperidinylmethanol (115 mg, 1 mmol), 5-bromo-3-(1-methylethyl)-1,2,4-thiadiazole (Example 182, Step 6, 207 mg, 1 mmol), triethylamine (0.42 mL, 3 mmol) and CH2Cl2 (3 mL) was stirred at ambient temperature overnight. The mixture was charged with additional 4-piperidinylmethanol (58 mg, 0.5 mmol) and was stirred at ambient temperature for 3 h. The mixture was charged with water, and extracted with CH2Cl2. The organics were dried over MgSO4, filtered, and the filtrate was concentrated. The crude product was purified by chromatography on a silica gel column using 0 to 10% MeOH/CH2Cl2 to give 159 mg (66%) of {1-[3-(1-methylethyl)-1,2,4-thiadiazol-5-yl]-4-piperidinyl}methanol as a golden oil. 1H NMR (400 MHz, CDCl3): δ 3.98-3.88 (m, 2H), 3.54 (d, 2H, J=6.3 Hz), 3.20-3.05 (m, 2H), 3.02 (septet, 1H, J=6.9 Hz), 1.90-1.80 (m, 2H), 1.82-1.70 (m, 1H), 1.42-1.25 (m, 8H); LRMS (ESI), m/z 242 (M+H).

Workup

  1. stirringwas stirred at ambient temperature for 3 h
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe crude product was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-75db5f5c5a1242ffac5482bbc17d87d1
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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