Triethylamine → 8-(3-Fluoropropyl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 532437Notes

Reaction equation

HRID 532437 reaction equation
[CH2:1]1[C@H:7]2[NH:8][C@H:3]([CH2:4][CH:5]([OH:9])[CH2:6]2)[CH2:2]1.Br[CH2:11][CH2:12][CH2:13][F:14].C(N(CC)CC)C>CN(C=O)C>[F:14][CH2:13][CH2:12][CH2:11][N:8]1[CH:7]2[CH2:1][CH2:2][CH:3]1[CH2:4][CH:5]([OH:9])[CH2:6]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67699Propane, 1-bromo-3-fluoro-HCID 73480Nortropine

Product 1

HCID 689414078-(3-Fluoropropyl)-8-azabicyclo[3.2.1]octan-3-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of nortropine (381.6 mg), 1-bromo-3-fluoropropane (634.4 mg) and triethylamine (0.42 ml) in DMF (7.5 ml) was heated to 60° C. and stirred at this temperature for 10 h. The solvent was then removed in vacuo. The product with the molecular weight of 187.26 (C10H18FNO) was obtained in this way; MS (ESI): 188 (M+H+).

Workup

  1. customThe solvent was then removed in vacuo
  2. customThe product with the molecular weight of 187.26 (C10H18FNO) was obtained in this way

Sources & evidence

ORD record
ord-a2c7dc60666d499b9c964627a2edf6d7
Source dataset
uspto-grants-2014_10
Patent number
US08853208B2

Reaction notes

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